There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 219989-84-1 | MDL No. : | MFCD04307791 |
Formula : | C27H42N2O5S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FABUFPQFXZVHFB-PVYNADRNSA-N |
M.W : | 506.70 | Pubchem ID : | 6445540 |
Synonyms : |
BMS-247550;Aza-epothilone B;Azaepothilone BBMS 2475501. Trade name: Ixempra.
|
Num. heavy atoms : | 35 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.74 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 144.19 |
TPSA : | 140.29 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.82 cm/s |
Log Po/w (iLOGP) : | 3.42 |
Log Po/w (XLOGP3) : | 3.62 |
Log Po/w (WLOGP) : | 3.56 |
Log Po/w (MLOGP) : | 1.22 |
Log Po/w (SILICOS-IT) : | 4.78 |
Consensus Log Po/w : | 3.32 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.24 |
Solubility : | 0.00294 mg/ml ; 0.00000581 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.25 |
Solubility : | 0.000282 mg/ml ; 0.000000557 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -5.09 |
Solubility : | 0.00408 mg/ml ; 0.00000805 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 6.4 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P272-P280-P285-P302+P352-P304+P341-P333+P313-P342+P311-P363-P501 | UN#: | 2811 |
Hazard Statements: | H317-H334 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42.8% | With 3,3-dimethyldioxirane In dichloromethane; acetone at -78 - -50℃; for 1.5 h; Inert atmosphere | Preparation of Ixabepilone To a 250-mL three-neck flask equipped with a stir bar was added 10.0 mL of deionized water, 10.0 mL of acetone and 2.50 g of NaHCO3. The resulting mixture was stirred vigorously in a 24° C. bath for 15 minutes. To this mixture was added 3 portions of potassium peroxymonosulfate (1.67 g) every 10-15 minutes under a reduced pressure (ca. 50-100 mmHg). DMDO was distilled out and obtained as an acetone solution after every addition of potassium peroxymonosulfate. Under a N2 atmosphere, DMDO (10 mL) was transferred to the solution of Ia (61 mg, 0.124 mmol) in dry DCM (2.0 mL) slowly using a cannula while controlling the solution temperature at -78° C. Then the reaction mixture was warmed up to -50° C. and stirred for 1.5 h. When TLC analysis indicated the reaction was complete, excess DMDO was quenched by adding dimethyl sulfide (0.1 mL) at -50° C., and the mixture was warmed to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc/n-heptane=2:1) to give ixabepilone (27 mg, yield: 42.8percent) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.00 (m, 1H), 6.96 (s, 1H), 6.55 (s, 1H), 4.66-4.64 (m, 1H), 4.43 (brs, 1H), 4.06-4.04 (m, 1H), 3.79 (m, 1H), 2.82-2.79 (m, 1H), 2.77 (brs, 1H), 2.69 (s, 3H), 2.52-2.39 (m, 2H), 2.48 (brs, 1H), 2.31-2.26 (dd, J=12.0, 4.0 Hz, 1H), 1.96 (t, J=8.0 Hz, 2H), 1.62-1.53 (m, 4H), 1.37 (m, 3H), 1.33 (s, 3H), 1.27 (s, 3H), 1.16 (d, J=4.0 Hz, 3H), 1.09 (s, 3H), 0.98 (d, J=8.0 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 220.8, 170.6, 165.0, 152.5, 138.0, 119.2, 116.0, 75.2, 73.6, 61.5, 61.2, 54.6, 52.7, 43.8, 40.4, 37.9, 31.9, 31.8, 30.7, 23.9, 23.0, 21.8, 21.0, 19.3, 17.3, 17.1, 14.4; LCMS 507.28 [M+H]. |
0.31 g | With 3-chloro-benzenecarboperoxoic acid In chloroform at -20 - -15℃; for 4 h; Inert atmosphere | Example-48: Preparation of (lS,3S,7S,10R,HS,12S,16R)-7,ll-dihydroxy- 8,8,10,12,16-pentamethyl-3-[(lE)-l-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-17-oxa- 4-azabicyclo [14.1.0] heptadecane-5,9-dione (Ixabepilone) Chloroform (45 ml) was added to (4S,7R,8S,9S,16S,Z)-4,8-dihydroxy-5,5,7,9,13- pentamethyl- 16-((E)- 1 -(2-methylthiazol-4-yl)prop- 1 -en-2-yl)azacyclohexadec- 13 -ene- 2,6-dione compound of formula G (0.43 gm) at 25-30°C under nitrogen atmosphere and stirred for 10 min at the same temperature. Cooled the reaction mixture to -15°C to -20°C and m-chloro perbenzoic acid (0.23 gm) was added and stirred for 4 hrs at the same temperature. Dichloromethane and 7percent aqueous sodium bicarbonate solution were added to the reaction mixture. Raised the temperature of the reaction mixture to 25-30°C and stirred for 15 min at the same temperature. Both the organic and aqueous layers were separated and the organic layer was washed with 7percent aqueous sodium bicarbonate solution, followed by with 25percent aqueous sodium sulfite solution and then finally with 5percent aqueous sodium chloride solution. Distilled off the solvent completely from the organic layer under reduced pressure. The obtained residue was purified by preparative HPLC to get the title compound. Yield: 0.31 gm; Purity by HPLC: 99.0percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.2 g | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide; acetonitrile at 0 - 30℃; for 12 h; Inert atmosphere | Example-52: Preparation of (lS,3S,7S,10R,HS,12S,16R)-7,ll-dihydroxy- 8,8,10,12,16-pentamethyl-3-[(lE)-l-methyl-2-(2-methyl-4-thiazolyl)ethenyI]-17-oxa- 4-azabicyclo[14.1.0]heptadecane-5,9-dione (Ixabepilone) A mixture of (3S,6R,7S,8S)-l l-((2R,3S)-3-((S,E)-2-amino-3-methyl-4-(2- methylthiazol-4-yl)but-3-enyl)-2-methyloxiran-2-yl)-3,7-dihydroxy-4,4,6,8-tetramethyl- 5-oxoundecanoic acid compound of formula K (3 gm) and dimethyl formamide (30 ml) was stirred for 10 min at 25-30°C under nitrogen atmosphere. Acetonitrile (480 ml) was added to the reaction mixture at 25-30°C. Cooled the reaction mixture to 0-5°C, 1- hydroxybenzotriazole (0.23 gm) and l-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.2 gm) were added. Raised the temperature of the reaction mixture to 25- 30°C and stirred for 12 hrs at the same temperature. Water and ethyl acetate were added to the reaction mixture at 25-30°C and stirred for 10 min at the same temperature. Both the organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate. Combined the organic layers and washed with water followed by with aqueous sodium bicarbonate solution and then finally with aqueous sodium chloride solution. Distilled off the solvent completely from the organic layer under reduced pressure and then high vacuum was applied to get the title compound. Yield: 3.2 gm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 47% 2: 9.1% | With n-butyllithium; tungsten(VI) chloride In tetrahydrofuran; hexane at 25℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With DMDO In dichloromethane at -78 - -50℃; for 1h; | |
42.8% | With 3,3-dimethyldioxirane In dichloromethane; acetone at -78 - -50℃; for 1.5h; Inert atmosphere; | 11.16.31 Preparation of Ixabepilone Preparation of Ixabepilone To a 250-mL three-neck flask equipped with a stir bar was added 10.0 mL of deionized water, 10.0 mL of acetone and 2.50 g of NaHCO3. The resulting mixture was stirred vigorously in a 24° C. bath for 15 minutes. To this mixture was added 3 portions of potassium peroxymonosulfate (1.67 g) every 10-15 minutes under a reduced pressure (ca. 50-100 mmHg). DMDO was distilled out and obtained as an acetone solution after every addition of potassium peroxymonosulfate. Under a N2 atmosphere, DMDO (10 mL) was transferred to the solution of Ia (61 mg, 0.124 mmol) in dry DCM (2.0 mL) slowly using a cannula while controlling the solution temperature at -78° C. Then the reaction mixture was warmed up to -50° C. and stirred for 1.5 h. When TLC analysis indicated the reaction was complete, excess DMDO was quenched by adding dimethyl sulfide (0.1 mL) at -50° C., and the mixture was warmed to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc/n-heptane=2:1) to give ixabepilone (27 mg, yield: 42.8%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.00 (m, 1H), 6.96 (s, 1H), 6.55 (s, 1H), 4.66-4.64 (m, 1H), 4.43 (brs, 1H), 4.06-4.04 (m, 1H), 3.79 (m, 1H), 2.82-2.79 (m, 1H), 2.77 (brs, 1H), 2.69 (s, 3H), 2.52-2.39 (m, 2H), 2.48 (brs, 1H), 2.31-2.26 (dd, J=12.0, 4.0 Hz, 1H), 1.96 (t, J=8.0 Hz, 2H), 1.62-1.53 (m, 4H), 1.37 (m, 3H), 1.33 (s, 3H), 1.27 (s, 3H), 1.16 (d, J=4.0 Hz, 3H), 1.09 (s, 3H), 0.98 (d, J=8.0 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 220.8, 170.6, 165.0, 152.5, 138.0, 119.2, 116.0, 75.2, 73.6, 61.5, 61.2, 54.6, 52.7, 43.8, 40.4, 37.9, 31.9, 31.8, 30.7, 23.9, 23.0, 21.8, 21.0, 19.3, 17.3, 17.1, 14.4; LCMS 507.28 [M+H]. |
0.31 g | With 3-chloro-benzenecarboperoxoic acid In chloroform at -20 - -15℃; for 4h; Inert atmosphere; | 48 Example-48: Preparation of (lS,3S,7S,10R,HS,12S,16R)-7,ll-dihydroxy- 8,8,10,12,16-pentamethyl-3-[(lE)-l-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-17-oxa- 4-azabicyclo [14.1.0] heptadecane-5,9-dione (Ixabepilone) Example-48: Preparation of (lS,3S,7S,10R,HS,12S,16R)-7,ll-dihydroxy- 8,8,10,12,16-pentamethyl-3-[(lE)-l-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-17-oxa- 4-azabicyclo [14.1.0] heptadecane-5,9-dione (Ixabepilone) Chloroform (45 ml) was added to (4S,7R,8S,9S,16S,Z)-4,8-dihydroxy-5,5,7,9,13- pentamethyl- 16-((E)- 1 -(2-methylthiazol-4-yl)prop- 1 -en-2-yl)azacyclohexadec- 13 -ene- 2,6-dione compound of formula G (0.43 gm) at 25-30°C under nitrogen atmosphere and stirred for 10 min at the same temperature. Cooled the reaction mixture to -15°C to -20°C and m-chloro perbenzoic acid (0.23 gm) was added and stirred for 4 hrs at the same temperature. Dichloromethane and 7% aqueous sodium bicarbonate solution were added to the reaction mixture. Raised the temperature of the reaction mixture to 25-30°C and stirred for 15 min at the same temperature. Both the organic and aqueous layers were separated and the organic layer was washed with 7% aqueous sodium bicarbonate solution, followed by with 25% aqueous sodium sulfite solution and then finally with 5% aqueous sodium chloride solution. Distilled off the solvent completely from the organic layer under reduced pressure. The obtained residue was purified by preparative HPLC to get the title compound. Yield: 0.31 gm; Purity by HPLC: 99.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With diphenyl-phosphinic acid; sodium hydrogencarbonate In N,N-dimethyl-formamide at 4℃; for 24h; | |
3.2 g | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide; acetonitrile at 0 - 30℃; for 12h; Inert atmosphere; | 52 Example-52: Preparation of (lS,3S,7S,10R,HS,12S,16R)-7,ll-dihydroxy- 8,8,10,12,16-pentamethyl-3-[(lE)-l-methyl-2-(2-methyl-4-thiazolyl)ethenyI]-17-oxa- 4-azabicyclo[14.1.0]heptadecane-5,9-dione (Ixabepilone) Example-52: Preparation of (lS,3S,7S,10R,HS,12S,16R)-7,ll-dihydroxy- 8,8,10,12,16-pentamethyl-3-[(lE)-l-methyl-2-(2-methyl-4-thiazolyl)ethenyI]-17-oxa- 4-azabicyclo[14.1.0]heptadecane-5,9-dione (Ixabepilone) A mixture of (3S,6R,7S,8S)-l l-((2R,3S)-3-((S,E)-2-amino-3-methyl-4-(2- methylthiazol-4-yl)but-3-enyl)-2-methyloxiran-2-yl)-3,7-dihydroxy-4,4,6,8-tetramethyl- 5-oxoundecanoic acid compound of formula K (3 gm) and dimethyl formamide (30 ml) was stirred for 10 min at 25-30°C under nitrogen atmosphere. Acetonitrile (480 ml) was added to the reaction mixture at 25-30°C. Cooled the reaction mixture to 0-5°C, 1- hydroxybenzotriazole (0.23 gm) and l-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.2 gm) were added. Raised the temperature of the reaction mixture to 25- 30°C and stirred for 12 hrs at the same temperature. Water and ethyl acetate were added to the reaction mixture at 25-30°C and stirred for 10 min at the same temperature. Both the organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate. Combined the organic layers and washed with water followed by with aqueous sodium bicarbonate solution and then finally with aqueous sodium chloride solution. Distilled off the solvent completely from the organic layer under reduced pressure and then high vacuum was applied to get the title compound. Yield: 3.2 gm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With N-ethyl-N,N-diisopropylamine In dichloromethane at 40℃; for 18h; | |
89% | With 1H-imidazole; dmap In N,N-dimethyl-formamide at 0 - 25℃; for 2.16667h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1: tetrahydrofuran / 1 h / 25 °C 2: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h 3: tetrahydrofuran / 19 h / 40 °C 4: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 5: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 6: 82 percent / p-TsOH / acetone / 22 h / 20 °C 7: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 8: TFA / CH2Cl2 / 2 h / 20 °C 9: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 10: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 11: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1: 85 percent / diphenylphosphoryl azide; DBU / toluene / 2 h / 2 - 25 °C 2: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h 3: tetrahydrofuran / 19 h / 40 °C 4: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 5: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 6: 82 percent / p-TsOH / acetone / 22 h / 20 °C 7: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 8: TFA / CH2Cl2 / 2 h / 20 °C 9: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 10: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 11: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h 2: tetrahydrofuran / 19 h / 40 °C 3: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 4: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 5: 82 percent / p-TsOH / acetone / 22 h / 20 °C 6: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 7: TFA / CH2Cl2 / 2 h / 20 °C 8: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 9: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 10: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1: 99 percent / aq. AcOH / tetrahydrofuran / 8 h / 20 °C 2: 85 percent / diphenylphosphoryl azide; DBU / toluene / 2 h / 2 - 25 °C 3: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h 4: tetrahydrofuran / 19 h / 40 °C 5: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 6: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 7: 82 percent / p-TsOH / acetone / 22 h / 20 °C 8: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 9: TFA / CH2Cl2 / 2 h / 20 °C 10: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 11: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 12: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 2: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 2: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 3: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 2: 82 percent / p-TsOH / acetone / 22 h / 20 °C 3: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 4: TFA / CH2Cl2 / 2 h / 20 °C 5: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 6: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 7: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: tetrahydrofuran / 19 h / 40 °C 2: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 3: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 4: 82 percent / p-TsOH / acetone / 22 h / 20 °C 5: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 6: TFA / CH2Cl2 / 2 h / 20 °C 7: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 8: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 9: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 2: TFA / CH2Cl2 / 2 h / 20 °C 3: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 4: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 5: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 82 percent / p-TsOH / acetone / 22 h / 20 °C 2: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 3: TFA / CH2Cl2 / 2 h / 20 °C 4: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 5: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 6: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: TFA / CH2Cl2 / 2 h / 20 °C 2: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 3: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 4: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h 2: tetrahydrofuran / 19 h / 40 °C 3: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 4: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 5: 82 percent / p-TsOH / acetone / 22 h / 20 °C 6: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 7: TFA / CH2Cl2 / 2 h / 20 °C 8: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 9: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 10: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 2: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 3: 82 percent / p-TsOH / acetone / 22 h / 20 °C 4: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 5: TFA / CH2Cl2 / 2 h / 20 °C 6: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 7: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 8: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 71 percent / PMe3; H2O / tetrahydrofuran; toluene / 2 h / 25 °C 2: 43 percent / DPPA; NaHCO3 / dimethylformamide / 24 h / 4 °C | ||
Multi-step reaction with 2 steps 1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 1.2: 1 h / 45 °C 2.1: triphenylphosphine / tetrahydrofuran / 14 h / 45 °C / Inert atmosphere 2.2: 4 h / 45 °C 3.1: sodium hydrogencarbonate; diphenyl phosphoryl azide / N,N-dimethyl-formamide / 24 h / 0 - 4 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 2: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With diphenyl phosphoryl azide; sodium hydrogencarbonate In N,N-dimethyl-formamide at 0 - 4℃; for 24h; Inert atmosphere; | 1.C A solution of Compound B (0.33 g, 0.63 mmol) in degassed DMF (250 mL) was treated with solid NaHC03 (0.42 g, 5.0 mmol) and diphenylphosphoryl azide (0.54 mL, 2.5 mmol) at 0° C. under Ar. The resulting suspension was stirred at 4° C for 24 h, diluted with phosphate buffer (250 mL, pH=7) at 0° C and extracted with EtOAc (5 x 100 mL). The organic extracts were combined and washed with 10% aqueous Li CI (2x125 mL), dried (Na2S04) and concentrated in vacuo. The residue was first purified by flash chromatography (Si02, 2.0x10 cm, 2-5% MeOH-CHCl3 gradient elution) and then repurified using a Chromatotron (2 mm Si02 GF rotor, 2-5% MeOH-CHCl3 gradient elution) to afford the title compound (0.13 g, 40%) as a colorless oil: 1H NMR (CDC13, 400 MHz) δ 6.98 (s, 1 H), 6.71 (d, 1H, NH, J=8.1 Hz), 6.56 (s, 1 H), 4.69-4.62 (m, 1 H), 4.18-4.12 (m, 1 H), 4.01-3.96 (m, 1 H), 3. 86 (s, 1 H), 3.38-3.34 (m, 1 H) , 2.82 (dd, 1 H, J=5.6, 6.0 Hz), 2.71 (s, 3 H), 2.58 (s, 1 H), 2.43 (dd, 1 H, J=9.0, 14.5 Hz), 3.34 (dd, 1 H, J=3.0, 14.5 Hz), 2.14 (s, 3 H), 2.05-1.92 (m, 2 H), 1.82-1.41 (a series of multiplets, 7 H), 1.35 (s, 3 H), 1.28 (s, 3 H), 1.18 (d, 3 H, J=6.8 Hz), 1.14 (s, 3 H), 1.00 (d, 3 H, J=6.8 Hz); MS (ESI +): 507.2 (M+H) +; MS(ESI -): 505.4 (M-H) -. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | Stage #1: phosgene; ixabepilone With triethylamine In dichloromethane; toluene for 0.5h; Stage #2: 2-(pyridin-2-yldisulfanyl)ethan-1-amine hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane; toluene for 1h; | 9 Synthesis of pyridin-2-yldisulfanyl ethyl amide derivative of Ixabepilone Synthesis of pyridin-2-yldisulfanyl ethyl amide derivative of Ixabepilone [1519] Ixabepilone (5 mg, 0.0099 mmol) was dissolved in dichloromethane (CH2Cl2, 1.5 mL). Triethylamine (TEA, 5.6 μL, 0.040 mmol) and 20% phosgene in toluene (9.8 μL, 0.020 mmol) were added to the mixture and stirred for h. The mixture was purged with Ar to remove any excess phosgene. Pyridine dithioethylamine hydrochloric salt (3.7 mg, 0.020 mmole) and DIEA (2.8μ, 0.020 mmole) were added and stirred for an additional hour (Scheme 37). It was then pumped down to dryness and purified by flash column chromatography with dichloromethane and methanol (9:1) to yield a white solid (5.2 mg, 49% Yield). It was confirmed by electron spray mass spectrometry (m/z expected 718.99; Found 741.48 M+Na). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diphenyl phosphoryl azide; sodium hydrogencarbonate In N,N-dimethyl-formamide at 0℃; for 24h; Inert atmosphere; | 5 Example 5 One pot reaction forming Ixabepilone from compound 2 according to scheme 1. In this example, Ixabepilone was formed in a one pot reaction by activation of the compound 2 (formula II) by activation using diphenyl phosphoryl azide as activation agent, resulting in the formation of compound 4 of scheme 1 , followed by spontaneous formation of Ixabepilone: 100 mg (1.0 eq) crude Epothilone B - acetic hydrazide adduct was dissolved in 80 ml dry and degassed DMF and cooled to 0° C under nitrogen gas. Then 7.7 eq sodium bicarbonate and subsequently 4.0 eq diphenyl phosphoryl azide was added and stirring at 0° C maintained for 24 h. The reaction mixture was then diluted with 80 ml of cold phosphate buffer solution and extracted with ethyl acetate. Subsequent washing of the organic layer with cold 10% aqueous LiCl and drying with Na2S04 followed by concentration in vacuo then furnished the crude product. HPLC - MS [Column: Xbridge C-18 (50x3.0mm, 3,5um), Mobil phase: A; 5.0mM NH4OAc B; AcN (Gradient), Time/B%: 0.01/10 0.5/10 4/90 8/90, Flow: 0.8ml/Min, MS: ESI; positive mode] : Ret. time: 4.55 (43%), m/z: 507 (M+l , 7%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 2.2: -50 - 20 °C 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 5.2: 0.5 h / 30 °C 5.3: 1 h / 30 °C 6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 6.2: 0.5 h / -60 - -50 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 2.2: -50 - 20 °C 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 5.2: 0.5 h / 30 °C 5.3: 1 h / 30 °C 6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 6.2: 0.42 h / -20 °C 6.3: 1 h / -20 - 10 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.2: 6 h / -78 °C / Inert atmosphere 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 5.2: 0.5 h / 30 °C 5.3: 1 h / 30 °C 6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 6.2: 0.5 h / -60 - -50 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Multi-step reaction with 11 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.2: 6 h / -78 °C / Inert atmosphere 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 5.2: 0.5 h / 30 °C 5.3: 1 h / 30 °C 6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 6.2: 0.42 h / -20 °C 6.3: 1 h / -20 - 10 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 2.2: -50 - 20 °C 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 5.2: 0.5 h / 30 °C 5.3: 1 h / 30 °C 6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 6.2: 0.5 h / -60 - -50 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 9.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 2.2: -50 - 20 °C 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 5.2: 0.5 h / 30 °C 5.3: 1 h / 30 °C 6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 6.2: 0.42 h / -20 °C 6.3: 1 h / -20 - 10 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 9.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 2.2: -50 - 20 °C 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 7.2: 0.5 h / -60 - -50 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 8.2: 0.5 h 8.3: 50 °C 9.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 2.2: -50 - 20 °C 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 5.2: 0.5 h / 30 °C 5.3: 1 h / 30 °C 6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 6.2: 0.5 h / -60 - -50 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 2.2: -50 - 20 °C 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 7.2: 0.42 h / -20 °C 7.3: 1 h / -20 - 10 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 8.2: 0.5 h 8.3: 50 °C 9.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 2.2: -50 - 20 °C 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 5.2: 0.5 h / 30 °C 5.3: 1 h / 30 °C 6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 6.2: 0.42 h / -20 °C 6.3: 1 h / -20 - 10 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.2: 6 h / -78 °C / Inert atmosphere 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 5.2: 0.5 h / 30 °C 5.3: 1 h / 30 °C 6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 6.2: 0.5 h / -60 - -50 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 9.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.2: 6 h / -78 °C / Inert atmosphere 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 5.2: 0.5 h / 30 °C 5.3: 1 h / 30 °C 6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 6.2: 0.42 h / -20 °C 6.3: 1 h / -20 - 10 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 9.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.2: 6 h / -78 °C / Inert atmosphere 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 5.2: 0.5 h / 30 °C 5.3: 1 h / 30 °C 6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 6.2: 0.5 h / -60 - -50 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.2: 6 h / -78 °C / Inert atmosphere 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 7.2: 0.5 h / -60 - -50 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 8.2: 0.5 h 8.3: 50 °C 9.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.2: 6 h / -78 °C / Inert atmosphere 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 5.2: 0.5 h / 30 °C 5.3: 1 h / 30 °C 6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 6.2: 0.42 h / -20 °C 6.3: 1 h / -20 - 10 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.2: 6 h / -78 °C / Inert atmosphere 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 7.2: 0.42 h / -20 °C 7.3: 1 h / -20 - 10 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 8.2: 0.5 h 8.3: 50 °C 9.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 13 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 2.2: -50 - 20 °C 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 5.2: 20 °C 6.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water; <i>tert</i>-butyl alcohol / 18 h / 0 - 20 °C 7.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 8.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 8.2: 0.08 h / -20 °C 8.3: 1 h / -20 - 10 °C 9.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1 h / 20 °C 9.2: 0.5 h 9.3: 0.5 h / 20 °C 10.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 12.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 13.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 13 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.2: 6 h / -78 °C / Inert atmosphere 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 5.2: 20 °C 6.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water; <i>tert</i>-butyl alcohol / 18 h / 0 - 20 °C 7.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 8.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 8.2: 0.08 h / -20 °C 8.3: 1 h / -20 - 10 °C 9.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1 h / 20 °C 9.2: 0.5 h 9.3: 0.5 h / 20 °C 10.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 12.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 13.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 13 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 2.2: -50 - 20 °C 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 7.2: 0.5 h / -60 - -50 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 8.2: 0.5 h 8.3: 50 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 10.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 12.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 13.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 13 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 2.2: -50 - 20 °C 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 7.2: 0.42 h / -20 °C 7.3: 1 h / -20 - 10 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 8.2: 0.5 h 8.3: 50 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 10.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 12.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 13.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 13 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 2.2: -50 - 20 °C 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 7.2: 0.5 h / -60 - -50 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 8.2: 0.5 h 8.3: 50 °C 9.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 10.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 12.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 13.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 13 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 2.2: -50 - 20 °C 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 7.2: 0.42 h / -20 °C 7.3: 1 h / -20 - 10 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 8.2: 0.5 h 8.3: 50 °C 9.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 10.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 12.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 13.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 13 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.2: 6 h / -78 °C / Inert atmosphere 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 7.2: 0.5 h / -60 - -50 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 8.2: 0.5 h 8.3: 50 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 10.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 12.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 13.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 13 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.2: 6 h / -78 °C / Inert atmosphere 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 7.2: 0.42 h / -20 °C 7.3: 1 h / -20 - 10 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 8.2: 0.5 h 8.3: 50 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 10.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 12.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 13.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 13 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.2: 6 h / -78 °C / Inert atmosphere 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 7.2: 0.5 h / -60 - -50 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 8.2: 0.5 h 8.3: 50 °C 9.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 10.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 12.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 13.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 13 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.2: 6 h / -78 °C / Inert atmosphere 3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 4.1: triethylamine / tetrahydrofuran / 20 °C 5.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 7.2: 0.42 h / -20 °C 7.3: 1 h / -20 - 10 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 8.2: 0.5 h 8.3: 50 °C 9.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 10.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 12.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 13.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 2.1: triethylamine / tetrahydrofuran / 20 °C 3.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 3.2: 0.5 h / 30 °C 3.3: 1 h / 30 °C 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 4.2: 0.5 h / -60 - -50 °C 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 5.2: 0.5 h 5.3: 50 °C 6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 7.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 10 steps 1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 2.1: triethylamine / tetrahydrofuran / 20 °C 3.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 3.2: 0.5 h / 30 °C 3.3: 1 h / 30 °C 4.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 4.2: 0.42 h / -20 °C 4.3: 1 h / -20 - 10 °C 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 5.2: 0.5 h 5.3: 50 °C 6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 7.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 10 steps 1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 2.1: triethylamine / tetrahydrofuran / 20 °C 3.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 4.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 5.2: 0.5 h / -60 - -50 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Multi-step reaction with 10 steps 1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 2.1: triethylamine / tetrahydrofuran / 20 °C 3.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 3.2: 0.5 h / 30 °C 3.3: 1 h / 30 °C 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 4.2: 0.5 h / -60 - -50 °C 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 5.2: 0.5 h 5.3: 50 °C 6.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 10 steps 1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 2.1: triethylamine / tetrahydrofuran / 20 °C 3.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 4.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 5.2: 0.42 h / -20 °C 5.3: 1 h / -20 - 10 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 10 steps 1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 2.1: triethylamine / tetrahydrofuran / 20 °C 3.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 3.2: 0.5 h / 30 °C 3.3: 1 h / 30 °C 4.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 4.2: 0.42 h / -20 °C 4.3: 1 h / -20 - 10 °C 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 5.2: 0.5 h 5.3: 50 °C 6.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 2.1: triethylamine / tetrahydrofuran / 20 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 3.2: 20 °C 4.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water; <i>tert</i>-butyl alcohol / 18 h / 0 - 20 °C 5.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 6.2: 0.08 h / -20 °C 6.3: 1 h / -20 - 10 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1 h / 20 °C 7.2: 0.5 h 7.3: 0.5 h / 20 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 2.1: triethylamine / tetrahydrofuran / 20 °C 3.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 4.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 5.2: 0.5 h / -60 - -50 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 8.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 2.1: triethylamine / tetrahydrofuran / 20 °C 3.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 4.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 5.2: 0.42 h / -20 °C 5.3: 1 h / -20 - 10 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 8.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 2.1: triethylamine / tetrahydrofuran / 20 °C 3.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 4.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 5.2: 0.5 h / -60 - -50 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 2.1: triethylamine / tetrahydrofuran / 20 °C 3.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 4.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 5.2: 0.42 h / -20 °C 5.3: 1 h / -20 - 10 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 9 steps 1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 2.1: triethylamine / tetrahydrofuran / 20 °C 3.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 3.2: 0.5 h / 30 °C 3.3: 1 h / 30 °C 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 4.2: 0.5 h / -60 - -50 °C 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 5.2: 0.5 h 5.3: 50 °C 6.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 9.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 9 steps 1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 2.1: triethylamine / tetrahydrofuran / 20 °C 3.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 3.2: 0.5 h / 30 °C 3.3: 1 h / 30 °C 4.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 4.2: 0.42 h / -20 °C 4.3: 1 h / -20 - 10 °C 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 5.2: 0.5 h 5.3: 50 °C 6.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 9.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 1.2: 0.5 h / 30 °C 1.3: 1 h / 30 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 2.2: 0.5 h / -60 - -50 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 3.2: 0.5 h 3.3: 50 °C 4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 5.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 7 steps 1.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 1.2: 0.5 h / 30 °C 1.3: 1 h / 30 °C 2.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 2.2: 0.42 h / -20 °C 2.3: 1 h / -20 - 10 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 3.2: 0.5 h 3.3: 50 °C 4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 5.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 8 steps 1.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 1.2: 0.5 h / 30 °C 1.3: 1 h / 30 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 2.2: 0.5 h / -60 - -50 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 3.2: 0.5 h 3.3: 50 °C 4.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 5.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Multi-step reaction with 8 steps 1.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 1.2: 0.5 h / 30 °C 1.3: 1 h / 30 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 2.2: 0.5 h / -60 - -50 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 3.2: 0.5 h 3.3: 50 °C 4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 5.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 8 steps 1.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 1.2: 0.5 h / 30 °C 1.3: 1 h / 30 °C 2.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 2.2: 0.42 h / -20 °C 2.3: 1 h / -20 - 10 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 3.2: 0.5 h 3.3: 50 °C 4.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 5.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 8 steps 1.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 1.2: 0.5 h / 30 °C 1.3: 1 h / 30 °C 2.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 2.2: 0.42 h / -20 °C 2.3: 1 h / -20 - 10 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 3.2: 0.5 h 3.3: 50 °C 4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 5.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 8 steps 1.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 2.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 3.2: 0.5 h / -60 - -50 °C 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 4.2: 0.5 h 4.3: 50 °C 5.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 6.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 8 steps 1.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 2.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 3.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 3.2: 0.42 h / -20 °C 3.3: 1 h / -20 - 10 °C 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 4.2: 0.5 h 4.3: 50 °C 5.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 6.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 9 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 1.2: 20 °C 2.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water; <i>tert</i>-butyl alcohol / 18 h / 0 - 20 °C 3.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 4.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 4.2: 0.08 h / -20 °C 4.3: 1 h / -20 - 10 °C 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1 h / 20 °C 5.2: 0.5 h 5.3: 0.5 h / 20 °C 6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 7.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 9 steps 1.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 2.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 3.2: 0.5 h / -60 - -50 °C 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 4.2: 0.5 h 4.3: 50 °C 5.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 9 steps 1.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 2.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 3.2: 0.5 h / -60 - -50 °C 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 4.2: 0.5 h 4.3: 50 °C 5.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 9 steps 1.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 2.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 3.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 3.2: 0.42 h / -20 °C 3.3: 1 h / -20 - 10 °C 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 4.2: 0.5 h 4.3: 50 °C 5.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 9 steps 1.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 2.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 3.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 3.2: 0.42 h / -20 °C 3.3: 1 h / -20 - 10 °C 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 4.2: 0.5 h 4.3: 50 °C 5.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 2.2: 0.5 h / -60 - -50 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 3.2: 0.5 h 3.3: 50 °C 4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 5.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 7 steps 1.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 2.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 2.2: 0.42 h / -20 °C 2.3: 1 h / -20 - 10 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 3.2: 0.5 h 3.3: 50 °C 4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 5.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 8 steps 1.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 2.2: 0.5 h / -60 - -50 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 3.2: 0.5 h 3.3: 50 °C 4.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 5.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Multi-step reaction with 8 steps 1.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 2.2: 0.5 h / -60 - -50 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 3.2: 0.5 h 3.3: 50 °C 4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 5.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 8 steps 1.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 2.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 2.2: 0.42 h / -20 °C 2.3: 1 h / -20 - 10 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 3.2: 0.5 h 3.3: 50 °C 4.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 5.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 8 steps 1.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 2.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 2.2: 0.42 h / -20 °C 2.3: 1 h / -20 - 10 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 3.2: 0.5 h 3.3: 50 °C 4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 5.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 1.2: 0.5 h / -60 - -50 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 2.2: 0.5 h 2.3: 50 °C 3.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 4.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 5.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 6.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 6 steps 1.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 1.2: 0.42 h / -20 °C 1.3: 1 h / -20 - 10 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 2.2: 0.5 h 2.3: 50 °C 3.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 4.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 5.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 6.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 7 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 1.2: 0.5 h / -60 - -50 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 2.2: 0.5 h 2.3: 50 °C 3.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 4.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 5.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 6.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Multi-step reaction with 7 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 1.2: 0.5 h / -60 - -50 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 2.2: 0.5 h 2.3: 50 °C 3.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 4.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 5.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 6.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 7 steps 1.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 1.2: 0.42 h / -20 °C 1.3: 1 h / -20 - 10 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 2.2: 0.5 h 2.3: 50 °C 3.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 4.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 5.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 6.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 7 steps 1.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 1.2: 0.42 h / -20 °C 1.3: 1 h / -20 - 10 °C 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 2.2: 0.5 h 2.3: 50 °C 3.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 4.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 5.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 6.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 1.2: -50 - 20 °C 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 4.2: 0.5 h / 30 °C 4.3: 1 h / 30 °C 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 5.2: 0.5 h / -60 - -50 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 10 steps 1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 1.2: -50 - 20 °C 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 4.2: 0.5 h / 30 °C 4.3: 1 h / 30 °C 5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 5.2: 0.42 h / -20 °C 5.3: 1 h / -20 - 10 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 10 steps 1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 6 h / -78 °C / Inert atmosphere 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 4.2: 0.5 h / 30 °C 4.3: 1 h / 30 °C 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 5.2: 0.5 h / -60 - -50 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Multi-step reaction with 10 steps 1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 6 h / -78 °C / Inert atmosphere 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 4.2: 0.5 h / 30 °C 4.3: 1 h / 30 °C 5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 5.2: 0.42 h / -20 °C 5.3: 1 h / -20 - 10 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 1.2: -50 - 20 °C 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 4.2: 0.5 h / 30 °C 4.3: 1 h / 30 °C 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 5.2: 0.5 h / -60 - -50 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 8.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 1.2: -50 - 20 °C 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 4.2: 0.5 h / 30 °C 4.3: 1 h / 30 °C 5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 5.2: 0.42 h / -20 °C 5.3: 1 h / -20 - 10 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 8.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 1.2: -50 - 20 °C 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 5.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 6.2: 0.5 h / -60 - -50 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 1.2: -50 - 20 °C 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 4.2: 0.5 h / 30 °C 4.3: 1 h / 30 °C 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 5.2: 0.5 h / -60 - -50 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 1.2: -50 - 20 °C 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 5.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 6.2: 0.42 h / -20 °C 6.3: 1 h / -20 - 10 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 1.2: -50 - 20 °C 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 4.2: 0.5 h / 30 °C 4.3: 1 h / 30 °C 5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 5.2: 0.42 h / -20 °C 5.3: 1 h / -20 - 10 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 6 h / -78 °C / Inert atmosphere 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 4.2: 0.5 h / 30 °C 4.3: 1 h / 30 °C 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 5.2: 0.5 h / -60 - -50 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 8.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 6 h / -78 °C / Inert atmosphere 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 4.2: 0.5 h / 30 °C 4.3: 1 h / 30 °C 5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 5.2: 0.42 h / -20 °C 5.3: 1 h / -20 - 10 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 8.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 6 h / -78 °C / Inert atmosphere 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 4.2: 0.5 h / 30 °C 4.3: 1 h / 30 °C 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 5.2: 0.5 h / -60 - -50 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 6 h / -78 °C / Inert atmosphere 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 5.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 6.2: 0.5 h / -60 - -50 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 6 h / -78 °C / Inert atmosphere 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 4.2: 0.5 h / 30 °C 4.3: 1 h / 30 °C 5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 5.2: 0.42 h / -20 °C 5.3: 1 h / -20 - 10 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 6.2: 0.5 h 6.3: 50 °C 7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 10.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 11 steps 1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 6 h / -78 °C / Inert atmosphere 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 5.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 6.2: 0.42 h / -20 °C 6.3: 1 h / -20 - 10 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 1.2: -50 - 20 °C 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 4.2: 20 °C 5.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water; <i>tert</i>-butyl alcohol / 18 h / 0 - 20 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 7.2: 0.08 h / -20 °C 7.3: 1 h / -20 - 10 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1 h / 20 °C 8.2: 0.5 h 8.3: 0.5 h / 20 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 1.2: -50 - 20 °C 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 5.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 6.2: 0.5 h / -60 - -50 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 9.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 1.2: -50 - 20 °C 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 5.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 6.2: 0.42 h / -20 °C 6.3: 1 h / -20 - 10 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 9.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 1.2: -50 - 20 °C 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 5.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 6.2: 0.5 h / -60 - -50 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere 1.2: -50 - 20 °C 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 5.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 6.2: 0.42 h / -20 °C 6.3: 1 h / -20 - 10 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 6 h / -78 °C / Inert atmosphere 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 4.2: 20 °C 5.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water; <i>tert</i>-butyl alcohol / 18 h / 0 - 20 °C 6.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 7.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 7.2: 0.08 h / -20 °C 7.3: 1 h / -20 - 10 °C 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1 h / 20 °C 8.2: 0.5 h 8.3: 0.5 h / 20 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 6 h / -78 °C / Inert atmosphere 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 5.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 6.2: 0.5 h / -60 - -50 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 9.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 6 h / -78 °C / Inert atmosphere 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 5.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 6.2: 0.42 h / -20 °C 6.3: 1 h / -20 - 10 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 9.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 6 h / -78 °C / Inert atmosphere 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 5.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 6.2: 0.5 h / -60 - -50 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 12 steps 1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 6 h / -78 °C / Inert atmosphere 2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: triethylamine / tetrahydrofuran / 20 °C 4.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 5.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 6.2: 0.42 h / -20 °C 6.3: 1 h / -20 - 10 °C 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 7.2: 0.5 h 7.3: 50 °C 8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 11.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 12.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: triethylamine / tetrahydrofuran / 20 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 2.2: 20 °C 3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water; <i>tert</i>-butyl alcohol / 18 h / 0 - 20 °C 4.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 5.2: 0.08 h / -20 °C 5.3: 1 h / -20 - 10 °C 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1 h / 20 °C 6.2: 0.5 h 6.3: 0.5 h / 20 °C 7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 10 steps 1.1: triethylamine / tetrahydrofuran / 20 °C 2.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 3.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 4.2: 0.5 h / -60 - -50 °C 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 5.2: 0.5 h 5.3: 50 °C 6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 7.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 10 steps 1.1: triethylamine / tetrahydrofuran / 20 °C 2.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 3.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 4.2: 0.5 h / -60 - -50 °C 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 5.2: 0.5 h 5.3: 50 °C 6.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Multi-step reaction with 10 steps 1.1: triethylamine / tetrahydrofuran / 20 °C 2.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 3.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 4.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 4.2: 0.42 h / -20 °C 4.3: 1 h / -20 - 10 °C 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 5.2: 0.5 h 5.3: 50 °C 6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 7.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 10 steps 1.1: triethylamine / tetrahydrofuran / 20 °C 2.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 3.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 4.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 4.2: 0.42 h / -20 °C 4.3: 1 h / -20 - 10 °C 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 5.2: 0.5 h 5.3: 50 °C 6.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 8 steps 1.1: triethylamine / tetrahydrofuran / 20 °C 2.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 2.2: 0.5 h / 30 °C 2.3: 1 h / 30 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 3.2: 0.5 h / -60 - -50 °C 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 4.2: 0.5 h 4.3: 50 °C 5.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 6.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 8 steps 1.1: triethylamine / tetrahydrofuran / 20 °C 2.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 2.2: 0.5 h / 30 °C 2.3: 1 h / 30 °C 3.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 3.2: 0.42 h / -20 °C 3.3: 1 h / -20 - 10 °C 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 4.2: 0.5 h 4.3: 50 °C 5.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 6.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 9 steps 1.1: triethylamine / tetrahydrofuran / 20 °C 2.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 2.2: 0.5 h / 30 °C 2.3: 1 h / 30 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 3.2: 0.5 h / -60 - -50 °C 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 4.2: 0.5 h 4.3: 50 °C 5.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 9 steps 1.1: triethylamine / tetrahydrofuran / 20 °C 2.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 2.2: 0.5 h / 30 °C 2.3: 1 h / 30 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 3.2: 0.5 h / -60 - -50 °C 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 4.2: 0.5 h 4.3: 50 °C 5.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 9 steps 1.1: triethylamine / tetrahydrofuran / 20 °C 2.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 2.2: 0.5 h / 30 °C 2.3: 1 h / 30 °C 3.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 3.2: 0.42 h / -20 °C 3.3: 1 h / -20 - 10 °C 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 4.2: 0.5 h 4.3: 50 °C 5.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 9 steps 1.1: triethylamine / tetrahydrofuran / 20 °C 2.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 3.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere 4.2: 0.5 h / -60 - -50 °C 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 5.2: 0.5 h 5.3: 50 °C 6.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 9.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 9 steps 1.1: triethylamine / tetrahydrofuran / 20 °C 2.1: 4-methylmorpholine N-oxide; potassium dioxido(dioxo)osmium hydrate / water; acetone / 3 h / 30 °C 2.2: 0.5 h / 30 °C 2.3: 1 h / 30 °C 3.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 3.2: 0.42 h / -20 °C 3.3: 1 h / -20 - 10 °C 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 4.2: 0.5 h 4.3: 50 °C 5.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 9.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere | ||
Multi-step reaction with 9 steps 1.1: triethylamine / tetrahydrofuran / 20 °C 2.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C 3.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C 4.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere 4.2: 0.42 h / -20 °C 4.3: 1 h / -20 - 10 °C 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C 5.2: 0.5 h 5.3: 50 °C 6.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C 7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C 9.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 18 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 1.2: 14 h / -75 - 30 °C 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 4.2: 0.75 h / -75 - -35 °C / Inert atmosphere 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 5.2: 2 h / 25 - 30 °C / Inert atmosphere 6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 7.2: 1 h / -78 °C 8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 13.2: 3 h / 0 - 30 °C / Inert atmosphere 14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 15.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 16.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 17.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 18.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 18 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 1.2: 14 h / -75 - 30 °C 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 4.2: 0.75 h / -75 - -35 °C / Inert atmosphere 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 5.2: 2 h / 25 - 30 °C / Inert atmosphere 6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 7.2: 1 h / -78 °C 8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 13.2: 3 h / 0 - 30 °C / Inert atmosphere 14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 15.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 16.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 17.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 18.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 19 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 1.2: 14 h / -75 - 30 °C 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 4.2: 0.75 h / -75 - -35 °C / Inert atmosphere 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 5.2: 2 h / 25 - 30 °C / Inert atmosphere 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 8.2: 1 h / -78 °C 9.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 14.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 14.2: 3 h / 0 - 30 °C / Inert atmosphere 15.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 16.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 17.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 18.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 19.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere |
Multi-step reaction with 19 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 1.2: 14 h / -75 - 30 °C 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 4.2: 0.75 h / -75 - -35 °C / Inert atmosphere 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 5.2: 2 h / 25 - 30 °C / Inert atmosphere 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 8.2: 1 h / -78 °C 9.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 14.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 14.2: 3 h / 0 - 30 °C / Inert atmosphere 15.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 16.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 17.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 18.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 19.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 19 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 1.2: 14 h / -75 - 30 °C 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 4.2: 0.75 h / -75 - -35 °C / Inert atmosphere 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 5.2: 2 h / 25 - 30 °C / Inert atmosphere 6.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 8.2: 1 h / -78 °C 9.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 14.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 14.2: 3 h / 0 - 30 °C / Inert atmosphere 15.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 16.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 17.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 18.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 19.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 19 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 1.2: 14 h / -75 - 30 °C 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 4.2: 0.75 h / -75 - -35 °C / Inert atmosphere 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 5.2: 2 h / 25 - 30 °C / Inert atmosphere 6.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 8.2: 1 h / -78 °C 9.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 14.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 14.2: 3 h / 0 - 30 °C / Inert atmosphere 15.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 16.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 17.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 18.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 19.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 24 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C 2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere 3.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 6.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 6.2: 2 h / 70 - 75 °C 7.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 7.2: 14 h / -75 - 30 °C 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 10.2: 0.75 h / -75 - -35 °C / Inert atmosphere 11.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 11.2: 2 h / 25 - 30 °C / Inert atmosphere 12.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 13.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 13.2: 1 h / -78 °C 14.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 15.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 16.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 17.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 19.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 19.2: 3 h / 0 - 30 °C / Inert atmosphere 20.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 21.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 22.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 23.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 24.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 24 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C 2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere 3.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 6.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 6.2: 2 h / 70 - 75 °C 7.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 7.2: 14 h / -75 - 30 °C 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 10.2: 0.75 h / -75 - -35 °C / Inert atmosphere 11.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 11.2: 2 h / 25 - 30 °C / Inert atmosphere 12.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 13.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 13.2: 1 h / -78 °C 14.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 15.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 16.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 17.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 19.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 19.2: 3 h / 0 - 30 °C / Inert atmosphere 20.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 21.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 22.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 23.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 24.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 25 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C 2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere 3.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 6.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 6.2: 2 h / 70 - 75 °C 7.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 7.2: 14 h / -75 - 30 °C 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 10.2: 0.75 h / -75 - -35 °C / Inert atmosphere 11.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 11.2: 2 h / 25 - 30 °C / Inert atmosphere 12.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 13.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 14.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 14.2: 1 h / -78 °C 15.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 16.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 17.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 18.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 19.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 20.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 20.2: 3 h / 0 - 30 °C / Inert atmosphere 21.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 22.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 23.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 24.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 25.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere |
Multi-step reaction with 25 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C 2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere 3.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 6.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 6.2: 2 h / 70 - 75 °C 7.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 7.2: 14 h / -75 - 30 °C 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 10.2: 0.75 h / -75 - -35 °C / Inert atmosphere 11.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 11.2: 2 h / 25 - 30 °C / Inert atmosphere 12.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 13.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 14.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 14.2: 1 h / -78 °C 15.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 16.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 17.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 18.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 19.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 20.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 20.2: 3 h / 0 - 30 °C / Inert atmosphere 21.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 22.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 23.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 24.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 25.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 25 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C 2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere 3.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 6.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 6.2: 2 h / 70 - 75 °C 7.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 7.2: 14 h / -75 - 30 °C 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 10.2: 0.75 h / -75 - -35 °C / Inert atmosphere 11.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 11.2: 2 h / 25 - 30 °C / Inert atmosphere 12.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 13.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 14.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 14.2: 1 h / -78 °C 15.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 16.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 17.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 18.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 19.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 20.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 20.2: 3 h / 0 - 30 °C / Inert atmosphere 21.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 22.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 23.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 24.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 25.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 25 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C 2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere 3.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 6.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 6.2: 2 h / 70 - 75 °C 7.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 7.2: 14 h / -75 - 30 °C 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 10.2: 0.75 h / -75 - -35 °C / Inert atmosphere 11.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 11.2: 2 h / 25 - 30 °C / Inert atmosphere 12.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 13.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 14.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 14.2: 1 h / -78 °C 15.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 16.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 17.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 18.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 19.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 20.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 20.2: 3 h / 0 - 30 °C / Inert atmosphere 21.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 22.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 23.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 24.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 25.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 23 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere 2.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 5.2: 2 h / 70 - 75 °C 6.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 6.2: 14 h / -75 - 30 °C 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 9.2: 0.75 h / -75 - -35 °C / Inert atmosphere 10.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 10.2: 2 h / 25 - 30 °C / Inert atmosphere 11.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 12.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 12.2: 1 h / -78 °C 13.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 14.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 15.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 16.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 18.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 18.2: 3 h / 0 - 30 °C / Inert atmosphere 19.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 20.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 21.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 22.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 23.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 23 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere 2.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 5.2: 2 h / 70 - 75 °C 6.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 6.2: 14 h / -75 - 30 °C 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 9.2: 0.75 h / -75 - -35 °C / Inert atmosphere 10.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 10.2: 2 h / 25 - 30 °C / Inert atmosphere 11.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 12.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 12.2: 1 h / -78 °C 13.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 14.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 15.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 16.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 18.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 18.2: 3 h / 0 - 30 °C / Inert atmosphere 19.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 20.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 21.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 22.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 23.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 24 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere 2.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 5.2: 2 h / 70 - 75 °C 6.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 6.2: 14 h / -75 - 30 °C 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 9.2: 0.75 h / -75 - -35 °C / Inert atmosphere 10.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 10.2: 2 h / 25 - 30 °C / Inert atmosphere 11.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 12.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 13.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 13.2: 1 h / -78 °C 14.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 15.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 16.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 17.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 19.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 19.2: 3 h / 0 - 30 °C / Inert atmosphere 20.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 21.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 22.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 23.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 24.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere |
Multi-step reaction with 24 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere 2.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 5.2: 2 h / 70 - 75 °C 6.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 6.2: 14 h / -75 - 30 °C 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 9.2: 0.75 h / -75 - -35 °C / Inert atmosphere 10.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 10.2: 2 h / 25 - 30 °C / Inert atmosphere 11.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 12.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 13.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 13.2: 1 h / -78 °C 14.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 15.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 16.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 17.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 19.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 19.2: 3 h / 0 - 30 °C / Inert atmosphere 20.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 21.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 22.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 23.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 24.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 24 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere 2.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 5.2: 2 h / 70 - 75 °C 6.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 6.2: 14 h / -75 - 30 °C 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 9.2: 0.75 h / -75 - -35 °C / Inert atmosphere 10.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 10.2: 2 h / 25 - 30 °C / Inert atmosphere 11.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 12.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 13.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 13.2: 1 h / -78 °C 14.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 15.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 16.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 17.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 19.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 19.2: 3 h / 0 - 30 °C / Inert atmosphere 20.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 21.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 22.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 23.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 24.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 24 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere 2.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 5.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 5.2: 2 h / 70 - 75 °C 6.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 6.2: 14 h / -75 - 30 °C 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 9.2: 0.75 h / -75 - -35 °C / Inert atmosphere 10.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 10.2: 2 h / 25 - 30 °C / Inert atmosphere 11.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 12.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 13.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 13.2: 1 h / -78 °C 14.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 15.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 16.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 17.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 19.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 19.2: 3 h / 0 - 30 °C / Inert atmosphere 20.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 21.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 22.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 23.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 24.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 22 steps 1.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 4.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 4.2: 2 h / 70 - 75 °C 5.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 5.2: 14 h / -75 - 30 °C 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 8.2: 0.75 h / -75 - -35 °C / Inert atmosphere 9.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 9.2: 2 h / 25 - 30 °C / Inert atmosphere 10.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 11.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 11.2: 1 h / -78 °C 12.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 13.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 14.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 15.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 17.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 17.2: 3 h / 0 - 30 °C / Inert atmosphere 18.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 19.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 20.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 21.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 22.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 22 steps 1.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 4.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 4.2: 2 h / 70 - 75 °C 5.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 5.2: 14 h / -75 - 30 °C 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 8.2: 0.75 h / -75 - -35 °C / Inert atmosphere 9.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 9.2: 2 h / 25 - 30 °C / Inert atmosphere 10.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 11.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 11.2: 1 h / -78 °C 12.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 13.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 14.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 15.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 17.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 17.2: 3 h / 0 - 30 °C / Inert atmosphere 18.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 19.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 20.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 21.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 22.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 23 steps 1.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 4.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 4.2: 2 h / 70 - 75 °C 5.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 5.2: 14 h / -75 - 30 °C 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 8.2: 0.75 h / -75 - -35 °C / Inert atmosphere 9.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 9.2: 2 h / 25 - 30 °C / Inert atmosphere 10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 12.2: 1 h / -78 °C 13.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 14.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 15.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 16.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 18.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 18.2: 3 h / 0 - 30 °C / Inert atmosphere 19.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 20.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 21.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 22.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 23.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere |
Multi-step reaction with 23 steps 1.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 4.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 4.2: 2 h / 70 - 75 °C 5.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 5.2: 14 h / -75 - 30 °C 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 8.2: 0.75 h / -75 - -35 °C / Inert atmosphere 9.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 9.2: 2 h / 25 - 30 °C / Inert atmosphere 10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 12.2: 1 h / -78 °C 13.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 14.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 15.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 16.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 18.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 18.2: 3 h / 0 - 30 °C / Inert atmosphere 19.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 20.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 21.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 22.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 23.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 23 steps 1.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 4.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 4.2: 2 h / 70 - 75 °C 5.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 5.2: 14 h / -75 - 30 °C 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 8.2: 0.75 h / -75 - -35 °C / Inert atmosphere 9.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 9.2: 2 h / 25 - 30 °C / Inert atmosphere 10.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 12.2: 1 h / -78 °C 13.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 14.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 15.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 16.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 18.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 18.2: 3 h / 0 - 30 °C / Inert atmosphere 19.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 20.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 21.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 22.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 23.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 23 steps 1.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C 2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 4.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 4.2: 2 h / 70 - 75 °C 5.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 5.2: 14 h / -75 - 30 °C 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 8.2: 0.75 h / -75 - -35 °C / Inert atmosphere 9.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 9.2: 2 h / 25 - 30 °C / Inert atmosphere 10.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 12.2: 1 h / -78 °C 13.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 14.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 15.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 16.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 18.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 18.2: 3 h / 0 - 30 °C / Inert atmosphere 19.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 20.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 21.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 22.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 23.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 21 steps 1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 3.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 3.2: 2 h / 70 - 75 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 4.2: 14 h / -75 - 30 °C 5.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 7.2: 0.75 h / -75 - -35 °C / Inert atmosphere 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 8.2: 2 h / 25 - 30 °C / Inert atmosphere 9.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 10.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 10.2: 1 h / -78 °C 11.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 12.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 13.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 14.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 16.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 16.2: 3 h / 0 - 30 °C / Inert atmosphere 17.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 18.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 19.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 20.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 21.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 21 steps 1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 3.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 3.2: 2 h / 70 - 75 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 4.2: 14 h / -75 - 30 °C 5.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 7.2: 0.75 h / -75 - -35 °C / Inert atmosphere 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 8.2: 2 h / 25 - 30 °C / Inert atmosphere 9.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 10.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 10.2: 1 h / -78 °C 11.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 12.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 13.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 14.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 16.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 16.2: 3 h / 0 - 30 °C / Inert atmosphere 17.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 18.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 19.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 20.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 21.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 22 steps 1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 3.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 3.2: 2 h / 70 - 75 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 4.2: 14 h / -75 - 30 °C 5.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 7.2: 0.75 h / -75 - -35 °C / Inert atmosphere 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 8.2: 2 h / 25 - 30 °C / Inert atmosphere 9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 11.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 11.2: 1 h / -78 °C 12.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 13.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 14.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 15.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 17.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 17.2: 3 h / 0 - 30 °C / Inert atmosphere 18.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 19.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 20.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 21.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 22.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere |
Multi-step reaction with 22 steps 1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 3.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 3.2: 2 h / 70 - 75 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 4.2: 14 h / -75 - 30 °C 5.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 7.2: 0.75 h / -75 - -35 °C / Inert atmosphere 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 8.2: 2 h / 25 - 30 °C / Inert atmosphere 9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 11.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 11.2: 1 h / -78 °C 12.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 13.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 14.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 15.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 17.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 17.2: 3 h / 0 - 30 °C / Inert atmosphere 18.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 19.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 20.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 21.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 22.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 22 steps 1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 3.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 3.2: 2 h / 70 - 75 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 4.2: 14 h / -75 - 30 °C 5.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 7.2: 0.75 h / -75 - -35 °C / Inert atmosphere 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 8.2: 2 h / 25 - 30 °C / Inert atmosphere 9.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 11.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 11.2: 1 h / -78 °C 12.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 13.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 14.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 15.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 17.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 17.2: 3 h / 0 - 30 °C / Inert atmosphere 18.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 19.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 20.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 21.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 22.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 22 steps 1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 3.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 3.2: 2 h / 70 - 75 °C 4.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 4.2: 14 h / -75 - 30 °C 5.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 7.2: 0.75 h / -75 - -35 °C / Inert atmosphere 8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 8.2: 2 h / 25 - 30 °C / Inert atmosphere 9.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 11.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 11.2: 1 h / -78 °C 12.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 13.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 14.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 15.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 17.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 17.2: 3 h / 0 - 30 °C / Inert atmosphere 18.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 19.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 20.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 21.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 22.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 20 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 2.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 2.2: 2 h / 70 - 75 °C 3.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 3.2: 14 h / -75 - 30 °C 4.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 6.2: 0.75 h / -75 - -35 °C / Inert atmosphere 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 7.2: 2 h / 25 - 30 °C / Inert atmosphere 8.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 9.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 9.2: 1 h / -78 °C 10.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 11.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 12.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 13.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 15.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 15.2: 3 h / 0 - 30 °C / Inert atmosphere 16.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 17.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 18.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 19.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 20.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 20 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 2.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 2.2: 2 h / 70 - 75 °C 3.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 3.2: 14 h / -75 - 30 °C 4.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 6.2: 0.75 h / -75 - -35 °C / Inert atmosphere 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 7.2: 2 h / 25 - 30 °C / Inert atmosphere 8.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 9.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 9.2: 1 h / -78 °C 10.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 11.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 12.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 13.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 15.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 15.2: 3 h / 0 - 30 °C / Inert atmosphere 16.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 17.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 18.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 19.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 20.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 21 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 2.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 2.2: 2 h / 70 - 75 °C 3.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 3.2: 14 h / -75 - 30 °C 4.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 6.2: 0.75 h / -75 - -35 °C / Inert atmosphere 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 7.2: 2 h / 25 - 30 °C / Inert atmosphere 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 9.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 10.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 10.2: 1 h / -78 °C 11.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 12.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 13.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 14.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 16.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 16.2: 3 h / 0 - 30 °C / Inert atmosphere 17.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 18.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 19.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 20.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 21.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere |
Multi-step reaction with 21 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 2.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 2.2: 2 h / 70 - 75 °C 3.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 3.2: 14 h / -75 - 30 °C 4.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 6.2: 0.75 h / -75 - -35 °C / Inert atmosphere 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 7.2: 2 h / 25 - 30 °C / Inert atmosphere 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 9.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 10.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 10.2: 1 h / -78 °C 11.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 12.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 13.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 14.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 16.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 16.2: 3 h / 0 - 30 °C / Inert atmosphere 17.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 18.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 19.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 20.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 21.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 21 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 2.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 2.2: 2 h / 70 - 75 °C 3.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 3.2: 14 h / -75 - 30 °C 4.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 6.2: 0.75 h / -75 - -35 °C / Inert atmosphere 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 7.2: 2 h / 25 - 30 °C / Inert atmosphere 8.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 9.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 10.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 10.2: 1 h / -78 °C 11.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 12.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 13.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 14.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 16.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 16.2: 3 h / 0 - 30 °C / Inert atmosphere 17.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 18.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 19.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 20.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 21.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 21 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere 2.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 2.2: 2 h / 70 - 75 °C 3.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 3.2: 14 h / -75 - 30 °C 4.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 6.2: 0.75 h / -75 - -35 °C / Inert atmosphere 7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 7.2: 2 h / 25 - 30 °C / Inert atmosphere 8.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 9.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 10.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 10.2: 1 h / -78 °C 11.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 12.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 13.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 14.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 16.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 16.2: 3 h / 0 - 30 °C / Inert atmosphere 17.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 18.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 19.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 20.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 21.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 19 steps 1.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 1.2: 2 h / 70 - 75 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 2.2: 14 h / -75 - 30 °C 3.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 5.2: 0.75 h / -75 - -35 °C / Inert atmosphere 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 6.2: 2 h / 25 - 30 °C / Inert atmosphere 7.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 8.2: 1 h / -78 °C 9.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 14.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 14.2: 3 h / 0 - 30 °C / Inert atmosphere 15.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 16.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 17.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 18.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 19.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 19 steps 1.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 1.2: 2 h / 70 - 75 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 2.2: 14 h / -75 - 30 °C 3.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 5.2: 0.75 h / -75 - -35 °C / Inert atmosphere 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 6.2: 2 h / 25 - 30 °C / Inert atmosphere 7.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 8.2: 1 h / -78 °C 9.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 14.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 14.2: 3 h / 0 - 30 °C / Inert atmosphere 15.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 16.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 17.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 18.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 19.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 20 steps 1.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 1.2: 2 h / 70 - 75 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 2.2: 14 h / -75 - 30 °C 3.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 5.2: 0.75 h / -75 - -35 °C / Inert atmosphere 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 6.2: 2 h / 25 - 30 °C / Inert atmosphere 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 8.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 9.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 9.2: 1 h / -78 °C 10.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 11.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 12.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 13.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 15.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 15.2: 3 h / 0 - 30 °C / Inert atmosphere 16.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 17.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 18.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 19.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 20.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere |
Multi-step reaction with 20 steps 1.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 1.2: 2 h / 70 - 75 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 2.2: 14 h / -75 - 30 °C 3.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 5.2: 0.75 h / -75 - -35 °C / Inert atmosphere 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 6.2: 2 h / 25 - 30 °C / Inert atmosphere 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 8.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 9.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 9.2: 1 h / -78 °C 10.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 11.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 12.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 13.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 15.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 15.2: 3 h / 0 - 30 °C / Inert atmosphere 16.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 17.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 18.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 19.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 20.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 20 steps 1.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 1.2: 2 h / 70 - 75 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 2.2: 14 h / -75 - 30 °C 3.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 5.2: 0.75 h / -75 - -35 °C / Inert atmosphere 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 6.2: 2 h / 25 - 30 °C / Inert atmosphere 7.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 8.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 9.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 9.2: 1 h / -78 °C 10.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 11.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 12.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 13.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 15.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 15.2: 3 h / 0 - 30 °C / Inert atmosphere 16.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 17.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 18.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 19.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 20.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 20 steps 1.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave 1.2: 2 h / 70 - 75 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 2.2: 14 h / -75 - 30 °C 3.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 5.2: 0.75 h / -75 - -35 °C / Inert atmosphere 6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 6.2: 2 h / 25 - 30 °C / Inert atmosphere 7.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 8.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 9.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 9.2: 1 h / -78 °C 10.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 11.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 12.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 13.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 15.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 15.2: 3 h / 0 - 30 °C / Inert atmosphere 16.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 17.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 18.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 19.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 20.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 17 steps 1.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 3.2: 0.75 h / -75 - -35 °C / Inert atmosphere 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 4.2: 2 h / 25 - 30 °C / Inert atmosphere 5.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 6.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 6.2: 1 h / -78 °C 7.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 9.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 10.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 12.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 12.2: 3 h / 0 - 30 °C / Inert atmosphere 13.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 14.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 15.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 16.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 17.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 17 steps 1.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 3.2: 0.75 h / -75 - -35 °C / Inert atmosphere 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 4.2: 2 h / 25 - 30 °C / Inert atmosphere 5.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 6.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 6.2: 1 h / -78 °C 7.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 9.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 10.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 12.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 12.2: 3 h / 0 - 30 °C / Inert atmosphere 13.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 14.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 15.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 16.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 17.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 18 steps 1.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 3.2: 0.75 h / -75 - -35 °C / Inert atmosphere 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 4.2: 2 h / 25 - 30 °C / Inert atmosphere 5.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 6.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 7.2: 1 h / -78 °C 8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 13.2: 3 h / 0 - 30 °C / Inert atmosphere 14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 15.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 16.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 17.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 18.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere |
Multi-step reaction with 18 steps 1.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 3.2: 0.75 h / -75 - -35 °C / Inert atmosphere 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 4.2: 2 h / 25 - 30 °C / Inert atmosphere 5.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 6.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 7.2: 1 h / -78 °C 8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 13.2: 3 h / 0 - 30 °C / Inert atmosphere 14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 15.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 16.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 17.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 18.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 18 steps 1.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 3.2: 0.75 h / -75 - -35 °C / Inert atmosphere 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 4.2: 2 h / 25 - 30 °C / Inert atmosphere 5.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 6.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 7.2: 1 h / -78 °C 8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 13.2: 3 h / 0 - 30 °C / Inert atmosphere 14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 15.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 16.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 17.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 18.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 18 steps 1.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 3.2: 0.75 h / -75 - -35 °C / Inert atmosphere 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 4.2: 2 h / 25 - 30 °C / Inert atmosphere 5.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 6.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 7.2: 1 h / -78 °C 8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 13.2: 3 h / 0 - 30 °C / Inert atmosphere 14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 15.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 16.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 17.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 18.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 16 steps 1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 2.2: 0.75 h / -75 - -35 °C / Inert atmosphere 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 3.2: 2 h / 25 - 30 °C / Inert atmosphere 4.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 5.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 5.2: 1 h / -78 °C 6.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 8.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 9.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 11.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 11.2: 3 h / 0 - 30 °C / Inert atmosphere 12.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 13.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 14.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 15.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 16.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 16 steps 1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 2.2: 0.75 h / -75 - -35 °C / Inert atmosphere 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 3.2: 2 h / 25 - 30 °C / Inert atmosphere 4.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 5.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 5.2: 1 h / -78 °C 6.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 8.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 9.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 11.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 11.2: 3 h / 0 - 30 °C / Inert atmosphere 12.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 13.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 14.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 15.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 16.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 17 steps 1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 2.2: 0.75 h / -75 - -35 °C / Inert atmosphere 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 3.2: 2 h / 25 - 30 °C / Inert atmosphere 4.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 5.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 6.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 6.2: 1 h / -78 °C 7.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 9.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 10.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 12.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 12.2: 3 h / 0 - 30 °C / Inert atmosphere 13.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 14.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 15.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 16.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 17.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere |
Multi-step reaction with 17 steps 1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 2.2: 0.75 h / -75 - -35 °C / Inert atmosphere 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 3.2: 2 h / 25 - 30 °C / Inert atmosphere 4.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 5.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 6.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 6.2: 1 h / -78 °C 7.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 9.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 10.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 12.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 12.2: 3 h / 0 - 30 °C / Inert atmosphere 13.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 14.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 15.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 16.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 17.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 17 steps 1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 2.2: 0.75 h / -75 - -35 °C / Inert atmosphere 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 3.2: 2 h / 25 - 30 °C / Inert atmosphere 4.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 5.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 6.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 6.2: 1 h / -78 °C 7.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 9.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 10.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 12.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 12.2: 3 h / 0 - 30 °C / Inert atmosphere 13.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 14.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 15.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 16.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 17.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 17 steps 1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 2.2: 0.75 h / -75 - -35 °C / Inert atmosphere 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 3.2: 2 h / 25 - 30 °C / Inert atmosphere 4.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 5.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 6.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 6.2: 1 h / -78 °C 7.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 9.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 10.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 12.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 12.2: 3 h / 0 - 30 °C / Inert atmosphere 13.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 14.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 15.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 16.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 17.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 15 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 1.2: 0.75 h / -75 - -35 °C / Inert atmosphere 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 2.2: 2 h / 25 - 30 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 4.2: 1 h / -78 °C 5.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 10.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 10.2: 3 h / 0 - 30 °C / Inert atmosphere 11.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 12.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 13.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 14.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 15.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 15 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 1.2: 0.75 h / -75 - -35 °C / Inert atmosphere 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 2.2: 2 h / 25 - 30 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 4.2: 1 h / -78 °C 5.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 10.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 10.2: 3 h / 0 - 30 °C / Inert atmosphere 11.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 12.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 13.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 14.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 15.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 16 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 1.2: 0.75 h / -75 - -35 °C / Inert atmosphere 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 2.2: 2 h / 25 - 30 °C / Inert atmosphere 3.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 4.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 5.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 5.2: 1 h / -78 °C 6.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 8.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 9.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 11.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 11.2: 3 h / 0 - 30 °C / Inert atmosphere 12.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 13.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 14.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 15.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 16.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere |
Multi-step reaction with 16 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 1.2: 0.75 h / -75 - -35 °C / Inert atmosphere 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 2.2: 2 h / 25 - 30 °C / Inert atmosphere 3.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 4.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 5.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 5.2: 1 h / -78 °C 6.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 8.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 9.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 11.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 11.2: 3 h / 0 - 30 °C / Inert atmosphere 12.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 13.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 14.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 15.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 16.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 16 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 1.2: 0.75 h / -75 - -35 °C / Inert atmosphere 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 2.2: 2 h / 25 - 30 °C / Inert atmosphere 3.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 4.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 5.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 5.2: 1 h / -78 °C 6.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 8.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 9.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 11.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 11.2: 3 h / 0 - 30 °C / Inert atmosphere 12.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 13.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 14.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 15.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 16.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 16 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 1.2: 0.75 h / -75 - -35 °C / Inert atmosphere 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 2.2: 2 h / 25 - 30 °C / Inert atmosphere 3.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 4.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 5.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 5.2: 1 h / -78 °C 6.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 8.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 9.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 11.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 11.2: 3 h / 0 - 30 °C / Inert atmosphere 12.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 13.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 14.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 15.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 16.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 14 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 1.2: 2 h / 25 - 30 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 3.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 3.2: 1 h / -78 °C 4.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 5.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 6.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 9.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 9.2: 3 h / 0 - 30 °C / Inert atmosphere 10.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 11.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 12.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 13.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 14.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 14 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 1.2: 2 h / 25 - 30 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 3.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 3.2: 1 h / -78 °C 4.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 5.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 6.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 9.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 9.2: 3 h / 0 - 30 °C / Inert atmosphere 10.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 11.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 12.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 13.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 14.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 15 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 1.2: 2 h / 25 - 30 °C / Inert atmosphere 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 3.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 4.2: 1 h / -78 °C 5.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 10.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 10.2: 3 h / 0 - 30 °C / Inert atmosphere 11.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 12.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 13.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 14.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 15.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere |
Multi-step reaction with 15 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 1.2: 2 h / 25 - 30 °C / Inert atmosphere 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 3.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 4.2: 1 h / -78 °C 5.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 10.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 10.2: 3 h / 0 - 30 °C / Inert atmosphere 11.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 12.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 13.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 14.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 15.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 15 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 1.2: 2 h / 25 - 30 °C / Inert atmosphere 2.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 3.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 4.2: 1 h / -78 °C 5.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 10.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 10.2: 3 h / 0 - 30 °C / Inert atmosphere 11.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 12.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 13.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 14.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 15.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 15 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 1.2: 2 h / 25 - 30 °C / Inert atmosphere 2.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 3.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 4.2: 1 h / -78 °C 5.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 10.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 10.2: 3 h / 0 - 30 °C / Inert atmosphere 11.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 12.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 13.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 14.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 15.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 14 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 1.2: 2 h / 25 - 30 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 3.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 3.2: 1 h / -78 °C 4.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 5.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 6.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 9.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 9.2: 3 h / 0 - 30 °C / Inert atmosphere 10.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 11.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 12.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 13.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 14.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 14 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 1.2: 2 h / 25 - 30 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 3.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 3.2: 1 h / -78 °C 4.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 5.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 6.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 9.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 9.2: 3 h / 0 - 30 °C / Inert atmosphere 10.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 11.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 12.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 13.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 14.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 15 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 1.2: 2 h / 25 - 30 °C / Inert atmosphere 2.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 3.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 4.2: 1 h / -78 °C 5.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 10.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 10.2: 3 h / 0 - 30 °C / Inert atmosphere 11.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 12.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 13.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 14.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 15.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere |
Multi-step reaction with 15 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 1.2: 2 h / 25 - 30 °C / Inert atmosphere 2.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 3.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 4.2: 1 h / -78 °C 5.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 10.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 10.2: 3 h / 0 - 30 °C / Inert atmosphere 11.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 12.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 13.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 14.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 15.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 17 steps 1.1: sodium tetrahydroborate / water; tetrahydrofuran / 3 h / 0 - 30 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 0 - 5 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 3.2: 2 h / 25 - 30 °C / Inert atmosphere 4.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 5.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 6.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 6.2: 1 h / -78 °C 7.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 9.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 10.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 12.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 12.2: 3 h / 0 - 30 °C / Inert atmosphere 13.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 14.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 15.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 16.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 17.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 17 steps 1.1: sodium tetrahydroborate / water; tetrahydrofuran / 3 h / 0 - 30 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 0 - 5 °C 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 3.2: 2 h / 25 - 30 °C / Inert atmosphere 4.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 5.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 6.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 6.2: 1 h / -78 °C 7.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 9.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 10.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 12.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 12.2: 3 h / 0 - 30 °C / Inert atmosphere 13.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 14.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 15.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 16.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 17.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 18 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 1.2: 14 h / -75 - 30 °C 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 4.2: 0.75 h / -75 - -35 °C / Inert atmosphere 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 5.2: 2 h / 25 - 30 °C / Inert atmosphere 6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 7.2: 1 h / -78 °C 8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 13.2: 3 h / 0 - 30 °C / Inert atmosphere 14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 15.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 16.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 17.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 18.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 18 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 1.2: 14 h / -75 - 30 °C 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 4.2: 0.75 h / -75 - -35 °C / Inert atmosphere 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 5.2: 2 h / 25 - 30 °C / Inert atmosphere 6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 7.2: 1 h / -78 °C 8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 13.2: 3 h / 0 - 30 °C / Inert atmosphere 14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 15.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 16.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 17.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 18.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 19 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 1.2: 14 h / -75 - 30 °C 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 4.2: 0.75 h / -75 - -35 °C / Inert atmosphere 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 5.2: 2 h / 25 - 30 °C / Inert atmosphere 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 8.2: 1 h / -78 °C 9.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 14.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 14.2: 3 h / 0 - 30 °C / Inert atmosphere 15.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 16.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 17.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 18.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 19.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere |
Multi-step reaction with 19 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 1.2: 14 h / -75 - 30 °C 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 4.2: 0.75 h / -75 - -35 °C / Inert atmosphere 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 5.2: 2 h / 25 - 30 °C / Inert atmosphere 6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 8.2: 1 h / -78 °C 9.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 14.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 14.2: 3 h / 0 - 30 °C / Inert atmosphere 15.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 16.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 17.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 18.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 19.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere | ||
Multi-step reaction with 19 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 1.2: 14 h / -75 - 30 °C 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 4.2: 0.75 h / -75 - -35 °C / Inert atmosphere 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 5.2: 2 h / 25 - 30 °C / Inert atmosphere 6.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 8.2: 1 h / -78 °C 9.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 14.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 14.2: 3 h / 0 - 30 °C / Inert atmosphere 15.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 16.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere 17.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere 18.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere 19.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere | ||
Multi-step reaction with 19 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere 1.2: 14 h / -75 - 30 °C 2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere 4.2: 0.75 h / -75 - -35 °C / Inert atmosphere 5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere 5.2: 2 h / 25 - 30 °C / Inert atmosphere 6.1: sodium tetrahydroborate; methanol / water / 2 h / 0 - 30 °C 7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere 8.2: 1 h / -78 °C 9.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere 10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C 11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere 12.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; <i>tert</i>-butyl alcohol / 2 h / 0 - 30 °C 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere 14.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 14.2: 3 h / 0 - 30 °C / Inert atmosphere 15.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere 16.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere 17.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 18.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 19.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: ixabepilone With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.166667h; Stage #2: octadecanedioic acid mono-triisopropylsilyl ester In dichloromethane at 0 - 20℃; | 13 Example 13 Ixabepilone-C18 Diacid Conjugate (IXB-FA18) To a stirring solution of ixabepilone (500 mg) in dry DCM (50 mL) at 0° C. is added DMAP (231 mg). After 5 minutes, EDC (137 mg) is added. After an additional 5 minutes, is added Mono-Tips Protected C18 Diacid (791 mg) and the resulting solution allowed to stir, and warm to room temperature overnight. The crude reaction mixture is then transferred to a separatory funnel and washed with water (3*50 mL), saturated NaCl (3*50 mL) and 0.1M HCl (3*50 mL). The organic phase is dried over MgSO4, and rotovapped to afford a yellowish-white solid. To remove the TIPS protecting group, the solid is taken up in THF and Bu4NF (1.2 g) is added and stirred. After 18 h, excess AMBERLITE ion exchange resin and excess CaCO3 are added to the reaction mixture. After 1 h, the solution is filtered and the filtrate is concentrated to a free-flowing oil. The oil is dissolved in 50 mL DCM, and upon addition of water a white precipitate forms. The reaction mixture is filtered and transferred to a separatory funnel, where it is extracted with water (3*50 mL). The organic phase is dried over MgSO4, filtered, and is concentrated to afford a solid. MS-Theoretical=803.16 [M-H]-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere; | 9.1 Step 1: Synthesis of Ixabepilone-ε-TROC-aminohexanoate (Scheme 1) Ixabepilone (20 mg, 0.039 mmol) and c-TROC-aminohexanoic acid (16.3 mg, 0.0585 mmol) will be dissolved in anhydrous DCM (10 mL) under N2. To the resulting clear solution, DCC (13.4 mg, 0.065 mmol) and DMAP (7.9 mg, 0.065 mmol) will be added (Scheme 1). The reaction mixture will then be stirred for 12 h at room temperature. The solvent will subsequently be evaporated and the resulting residue dissolved in a minimum amount of chloroform. The desired C-3 and C-7 derivatives can be isolated via purification using flash column chromatography with chloroform/methanol as the mobile phase. The derivatives are to be analyzed by electron spray mass spectroscopy (m/z), HPLC and 1H-NMR. The C-3 derivative of Ixabepilone-ε-TROC-aminohexanoate is used as an example in the following synthetic steps. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; | 9.1 Step 1: Synthesis of 3-tert-butyldimethylsilylIxabepilone or 7-tert-butyldimethylsilyl Ixabepilone Ixabepilone (20 mg, 0.039 mmol) and tert-butyldimethylsilyl chloride (8.3 mg, 0.055 mmol) will be mixed in anhydrous DMF (5 mE) under N2 atm. To the resulting clear solution, imidazole (10.7 mg, 0.158 mmol) will be added (Scheme 4) and the reaction will be allowed to stir at ambient temperature for 24 h. The solvent will be evaporated and the residue dissolved in a minimum amount of chloroform. The desired C-3 and C-7 derivatives will be isolated following purification of the crude product via flash colunm chromatography with chloroformlmethanol as the mobile phase. The derivatives will be analyzed by electron spray mass spectroscopy (mlz), HPEC and ‘H-NMR. The C-3 derivative of T135-Ixabepilone is used as an example in the following synthetic steps. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 2.17 h / 0 - 25 °C / Inert atmosphere 2: n-butyllithium; tungsten(VI) chloride / tetrahydrofuran; hexane / 1 h / -20 - 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 2.17 h / 0 - 25 °C / Inert atmosphere 2: n-butyllithium; tungsten(VI) chloride / tetrahydrofuran; hexane / 1 h / -20 - 0 °C / Inert atmosphere 3: dmap; triethylamine / toluene / 2 h / 0 - 25 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 2.17 h / 0 - 25 °C / Inert atmosphere 2: n-butyllithium; tungsten(VI) chloride / tetrahydrofuran; hexane / 1 h / -20 - 0 °C / Inert atmosphere 3: dmap; triethylamine / toluene / 2 h / 0 - 25 °C / Inert atmosphere 4: sodium iodide / tetrahydrofuran / 2 h / 60 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 2.17 h / 0 - 25 °C / Inert atmosphere 2: n-butyllithium; tungsten(VI) chloride / tetrahydrofuran; hexane / 1 h / -20 - 0 °C / Inert atmosphere 3: dmap; triethylamine / toluene / 2 h / 0 - 25 °C / Inert atmosphere 4: sodium iodide / tetrahydrofuran / 2 h / 60 °C / Inert atmosphere; Sealed tube 5: pyridine hydrogenfluoride / tetrahydrofuran / 1.5 h / 0 - 25 °C / Inert atmosphere |
Tags: 219989-84-1 synthesis path| 219989-84-1 SDS| 219989-84-1 COA| 219989-84-1 purity| 219989-84-1 application| 219989-84-1 NMR| 219989-84-1 COA| 219989-84-1 structure
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :