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CAS No. : | 6322-07-2 | MDL No. : | MFCD00005391 |
Formula : | C6H10O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SXZYCXMUPBBULW-LECHCGJUSA-N |
M.W : | 178.14 | Pubchem ID : | 165105 |
Synonyms : |
D-Gulono-1,4-lactone;D-Gulonic acid γ-lactone;NSC 34392;D-Gulono γ-lactone;D-Gulonic Acid-1,4-lactone
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.83 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 34.77 |
TPSA : | 107.22 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -8.83 cm/s |
Log Po/w (iLOGP) : | 0.07 |
Log Po/w (XLOGP3) : | -2.03 |
Log Po/w (WLOGP) : | -3.01 |
Log Po/w (MLOGP) : | -2.49 |
Log Po/w (SILICOS-IT) : | -1.53 |
Consensus Log Po/w : | -1.8 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.47 |
Solubility : | 521.0 mg/ml ; 2.93 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 0.3 |
Solubility : | 358.0 mg/ml ; 2.01 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 1.92 |
Solubility : | 14900.0 mg/ml ; 83.4 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.3 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
98% | With pyridine; 1H-imidazole at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 4 A molecular sieve; toluene-4-sulfonic acid In benzene for 10h; Heating; | |
With toluene-4-sulfonic acid In benzene for 10h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In benzene at 90℃; | |
100% | In benzene byproducts: H2O; triethylboroxine droped to a soln. of the lactone at 90°C over 4 h, H20 removed with a stream of inert gas; concd. (60°C, 1E-3 torr); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With pyridine In acetone at 0℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With pyridine In acetone at 0℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With toluene-4-sulfonic acid In acetone for 24h; | 1 p-Toluenesulfonic acid-monohydrate (1 g) was added to a stirred solution of D-gulono-lactone (20 g, 0.11 mol) in 2.2-dimethoxypropane (60 mL) and dry acetone (200 mL). After 24 hr t.l.c. (ethyl acetate) showed the consumption of starting material (Rf 0.0) and the formation of a major product (Rf 0.8). The reaction mixture was neutralized by stirring with excess sodium hydrogen carbonate, filtered and the solvent removed under reduced pressure. The residue was crystallized from ethyl acetate/hexane to give 2.3;5,6-Di-O-isopropylidene-D-gulono-1,4-lactone as white crystals (26.3 g, 0.1 mol, 91 % yield). M.p. 150-153°C; [α]D22 +76.2 (c. 0.88 in acetone); δH (200 MHz, CDCl3): 1.28 (s, 6H, C(CH3)2), 1.33, 1.37 (2 x s, 6H, C(CH3)2), 3.90 (dd. 1H, J 6.0 Hz, J 9.0 Hz), 4.02 - 4.10 (m, 1H), 4.18 - 4.27 (m, 1H), 4.49 (dd. 1 H, J3,4 3 Hz, J4,5 9 Hz, H-4), 4.92 (dd, 1H, J2,3 6 Hz, J3,4 3 Hz, H-3), 4.96 (d, 1H, J2.3 6 Hz. H-2): δc (50 MHz. CDCl3): 25.6 (C(CH3)2), 26.3 (C(CH3)2), 27.1 (C(CH3)2), 27.2 (C(CH3)2). 65.6 (CH2, C-2), 75.7, 76.4, 76.5. 81.3 (4 x CH, C-2, C-3, C-4), 110.9 (C(CH3)2), 114.7 (C(CH3)2). 173.3 (C=O). |
90% | With toluene-4-sulfonic acid In acetone | |
87% | With toluene-4-sulfonic acid In N,N-dimethyl-formamide; acetone; acetonitrile at 20℃; for 72h; Inert atmosphere; |
85% | With toluene-4-sulfonic acid In acetone for 48h; Ambient temperature; | |
82% | With toluene-4-sulfonic acid In acetone for 36h; | |
69% | With toluene-4-sulfonic acid In acetone at 23℃; for 24h; | |
With toluene-4-sulfonic acid In acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sulfuric acid; copper(II) sulfate for 12h; | |
98% | With copper(II) sulfate at 20℃; for 24h; | 1; 1.a; 2 20.2 g of D-gulonic γ-lactone (0.114 mol) and 27 g of anhydrous copper(II) sulfate (0.170 mol) were suspended in 0.65 L of dry acetone at ambient temperature, and 1.7 mL of concentrated sulfuric acid were added, which was then stirred for 24 h. The acidity was adjusted to 7 with calcium hydroxide, and then precipitated solids were filtered off. The resulting filtrate was concentrated under reduced pressure to obtain 28.7 g of (2R,3S,4S,5R)-2,3:5,6-di-O-isopropylidene-D-gulono-1,4-lactone compound (yield: 98%) as an oil, which was used immediately for the next reaction.To a stirred slurry of D-gulonic-γ-lactone 106 (20.2 g, 113.5 mmol) and anhydrous CuSO4 (27.0 g, 169.8 mmol) in dry acetone (650 mL) was added conc. H2SO4 (1.7 mL), and the mixture was stirred for 24 h at room temperature. The pH of the solution was adjusted to 7 with Ca(OH)2, and the resulting slurry was filtered and evaporated in vacuo to afford the diacetonide 107 (28.7 g, 98%) as a light-yellow syrup. It was used in the next step without further purification. To a stirred solution of diacetonide 107 (25.1 g, 97.2 mmol) in ether (450 mL) was added, cautiously in several portions, lithium aluminum hydride (7.2 g, 190.4 mmol) at 0° C., and the reaction mixture was stirred at room temperature for 10 h. After cooling, the reaction mixture was sequentially treated with water (7.2 mL), 15% aqueous sodium hydroxide solution (7.2 mL), water (21.6 mL), and MgSO4 (19 g), filtered and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1) to give the diol (24.1 g, 95%) as a syrup: 1H NMR (CDCl3) δ 1.29 (s, 3H, CH3),1.29 (s, 3H, CH3), 1.36 (s, 3H, CH3),1.43 (s, 3H, CH3),3.26 (s, 1H, OH), 3.28 (s, 1H, OH), 3.36-3.79 (m, 4H, HOCH2, OCH2), 3.96-4.03 (m, 2H, HOCH2CH(OR)R', OCHRR'), 4.12-4.22 (m, 2H); Anal. Calcd for C12H22O6: C, 54.95; H, 8.45. Found: C, 54.67; H, 8.4. |
97% | With sulfuric acid; copper(II) sulfate at 20℃; |
93% | With sulfonic acid; copper(II) sulfate for 18h; Ambient temperature; | |
90% | for 72h; | |
88% | With sulfuric acid; copper(II) sulfate at 20℃; for 24h; | |
70% | With hydrogenchloride for 18h; Ambient temperature; | |
66% | With sulfuric acid for 24h; | |
30% | With sulfuric acid; copper(II) sulfate at 20℃; for 18h; | |
With sulfuric acid; copper(II) sulfate at 20℃; for 24h; | ||
With sulfuric acid for 48h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With silver(l) oxide In water at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: 2,2-dimethoxy-propane; D-gulono-1,4-lactone With toluene-4-sulfonic acid In methanol; acetone at 20℃; for 2h; Stage #2: With sodium tetrahydroborate In ethanol for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With carbon tetrabromide; triphenylphosphine at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 90 percent / p-toluenesulfonic acid / acetone 2: 77 percent / sodium borohydride / tetrahydrofuran; methanol | ||
Multi-step reaction with 2 steps 1: CuSO4; H2SO4 / 24 h / 20 °C 2: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C | ||
Multi-step reaction with 2 steps 1: CuSO4; H2SO4 / 24 h / 20 °C 2: 24.1 g / NaBH4 / methanol / 2 h / 20 °C |
Multi-step reaction with 2 steps 1: 85 percent / p-toluenesulphonic acid / acetone / 48 h / Ambient temperature 2: 87 percent / lithium aluminum hydride / tetrahydrofuran; diethyl ether / 0.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 90 percent / p-toluenesulfonic acid / acetone 2: 77 percent / sodium borohydride / tetrahydrofuran; methanol 3: 75 percent / pyridine / CH2Cl2 / 6.5 h / 0 - 20 °C | ||
Multi-step reaction with 3 steps 1: CuSO4; H2SO4 / 24 h / 20 °C 2: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3: 98 percent / pyridine / 4 h / 0 °C | ||
Multi-step reaction with 3 steps 1: CuSO4; H2SO4 / 24 h / 20 °C 2: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C |
Multi-step reaction with 3 steps 1: 85 percent / p-toluenesulphonic acid / acetone / 48 h / Ambient temperature 2: 87 percent / lithium aluminum hydride / tetrahydrofuran; diethyl ether / 0.5 h / Ambient temperature 3: 100 percent / 4,4-dimethylaminopyridine / pyridine / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 90 percent / p-toluenesulfonic acid / acetone 2: 77 percent / sodium borohydride / tetrahydrofuran; methanol 3: 75 percent / pyridine / CH2Cl2 / 6.5 h / 0 - 20 °C 4: 92 percent / Na2S*9H2O / dimethylformamide / 12 h / 90 °C | ||
Multi-step reaction with 4 steps 1: CuSO4; H2SO4 / 24 h / 20 °C 2: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3: 98 percent / pyridine / 4 h / 0 °C 4: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C | ||
Multi-step reaction with 4 steps 1: CuSO4; H2SO4 / 24 h / 20 °C 2: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 65 percent / NH3 / ethanol / 24 h / 50 °C | ||
Multi-step reaction with 12 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 65 percent / NH3 / ethanol / 24 h / 50 °C | ||
Multi-step reaction with 12 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 65 percent / ethanolic NH3 / 24 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 19 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 12.1: 80 percent / pyridine / 12 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: K2CO3 / acetone / 2 h / 20 °C 18.1: 80 mg / tetrahydrofuran / 24 h / 20 °C 19.1: 69 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C | ||
Multi-step reaction with 18 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 12.1: aq. AcOH / 12 h / 70 °C 13.1: pyridine / 5 h / 50 °C 14.1: NaOMe / methanol / 4 h / 20 °C 15.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 16.1: K2CO3 / acetone / 2 h / 20 °C 17.1: 80 mg / tetrahydrofuran / 24 h / 20 °C 18.1: 69 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C | ||
Multi-step reaction with 20 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: aq. AcOH / 12 h / 70 °C 15.1: pyridine / 5 h / 50 °C 16.1: NaOMe / methanol / 4 h / 20 °C 17.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 18.1: K2CO3 / acetone / 2 h / 20 °C 19.1: 80 mg / tetrahydrofuran / 24 h / 20 °C 20.1: 69 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C |
Multi-step reaction with 19 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: K2CO3 / acetone / 2 h / 20 °C 18.1: 80 mg / tetrahydrofuran / 24 h / 20 °C 19.1: 69 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C | ||
Multi-step reaction with 20 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 65 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: 98 percent / aq. AcOH 15.1: pyridine / 5 h / 50 °C 16.1: 169 mg / sodium methoxide; methanol / 4 h / 20 °C 17.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 18.1: K2CO3 / acetone / 2 h / 20 °C 19.1: 80 mg / tetrahydrofuran / 24 h / 20 °C 20.1: 69 percent / TBAF / tetrahydrofuran / 1 h / 20 °C | ||
Multi-step reaction with 19 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 32 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 98 percent / aq. AcOH 14.1: pyridine / 5 h / 50 °C 15.1: 169 mg / sodium methoxide; methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: K2CO3 / acetone / 2 h / 20 °C 18.1: 80 mg / tetrahydrofuran / 24 h / 20 °C 19.1: 69 percent / TBAF / tetrahydrofuran / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 17 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 70 percent / Et3N / ethanol / 24 h / 20 °C 12.1: aq. AcOH / 12 h / 70 °C 13.1: pyridine / 5 h / 50 °C 14.1: NaOMe / methanol / 4 h / 20 °C 15.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 16.1: N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide; 1-hydroxybenzotriazole; N,N-diisopropylethylamine / CH2Cl2 / 12 h / 20 °C 17.1: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C | ||
Multi-step reaction with 18 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 70 percent / Et3N / ethanol / 24 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide; 1-hydroxybenzotriazole; N,N-diisopropylethylamine / CH2Cl2 / 12 h / 20 °C 18.1: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C | ||
Multi-step reaction with 20 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 20 percent / tetrahydrofuran / 24 h / 20 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: 98 percent / aq. AcOH 15.1: pyridine / 5 h / 50 °C 16.1: 134 mg / sodium methoxide; methanol / 4 h / 20 °C 17.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 18.1: K2CO3 / acetone / 2 h / 20 °C 19.1: 48 mg / tetrahydrofuran / 24 h / 20 °C 20.1: 65 percent / TBAF / tetrahydrofuran / 1 h / 20 °C |
Multi-step reaction with 19 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 70 percent / tetrahydrofuran / 24 h / 20 °C 13.1: 98 percent / aq. AcOH 14.1: pyridine / 5 h / 50 °C 15.1: 134 mg / sodium methoxide; methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: K2CO3 / acetone / 2 h / 20 °C 18.1: 48 mg / tetrahydrofuran / 24 h / 20 °C 19.1: 65 percent / TBAF / tetrahydrofuran / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C | ||
Multi-step reaction with 11 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C | ||
Multi-step reaction with 11 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 6.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C | ||
Multi-step reaction with 11 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C | ||
Multi-step reaction with 11 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 70 percent / Et3N / ethanol / 24 h / 20 °C 12.1: aq. AcOH / 12 h / 70 °C | ||
Multi-step reaction with 13 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 70 percent / Et3N / ethanol / 24 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C | ||
Multi-step reaction with 14 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 20 percent / tetrahydrofuran / 24 h / 20 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: 98 percent / aq. AcOH |
Multi-step reaction with 13 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 70 percent / tetrahydrofuran / 24 h / 20 °C 13.1: 98 percent / aq. AcOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 70 percent / Et3N / ethanol / 24 h / 20 °C | ||
Multi-step reaction with 12 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 70 percent / Et3N / ethanol / 24 h / 20 °C | ||
Multi-step reaction with 13 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 20 percent / tetrahydrofuran / 24 h / 20 °C 13.1: 80 percent / pyridine / 12 h / 20 °C |
Multi-step reaction with 12 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 70 percent / tetrahydrofuran / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 12.1: 80 percent / pyridine / 12 h / 20 °C | ||
Multi-step reaction with 11 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 32 percent / NH3 / ethanol / 24 h / 50 °C | ||
Multi-step reaction with 13 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C |
Multi-step reaction with 12 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 32 percent / NH3 / ethanol / 24 h / 50 °C | ||
Multi-step reaction with 13 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 65 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C | ||
Multi-step reaction with 12 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 32 percent / ethanolic NH3 / 24 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 13 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 12.1: 80 percent / pyridine / 12 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C | ||
Multi-step reaction with 12 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 12.1: aq. AcOH / 12 h / 70 °C | ||
Multi-step reaction with 14 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: aq. AcOH / 12 h / 70 °C |
Multi-step reaction with 13 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 13.1: aq. AcOH / 12 h / 70 °C | ||
Multi-step reaction with 14 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 65 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: 98 percent / aq. AcOH | ||
Multi-step reaction with 13 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 32 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 98 percent / aq. AcOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 17 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 90 percent / Et3N / ethanol / 24 h / 20 °C 12.1: aq. AcOH / 12 h / 70 °C 13.1: pyridine / 5 h / 50 °C 14.1: NaOMe / methanol / 4 h / 20 °C 15.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 16.1: N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide; 1-hydroxybenzotriazole; N,N-diisopropylethylamine / CH2Cl2 / 12 h / 20 °C 17.1: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C | ||
Multi-step reaction with 18 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 90 percent / Et3N / ethanol / 24 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide; 1-hydroxybenzotriazole; N,N-diisopropylethylamine / CH2Cl2 / 12 h / 20 °C 18.1: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C | ||
Multi-step reaction with 19 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 90 percent / Et3N / ethanol / 72 h / 20 °C 13.1: 99 percent / aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: 420 mg / sodium methoxide; methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: K2CO3 / acetone / 2 h / 20 °C 18.1: 99 mg / tetrahydrofuran / 24 h / 20 °C 19.1: 63 percent / TBAF / tetrahydrofuran / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 17 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 12.1: 80 percent / pyridine / 12 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: K2CO3 / acetone / 2 h / 20 °C | ||
Multi-step reaction with 16 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 12.1: aq. AcOH / 12 h / 70 °C 13.1: pyridine / 5 h / 50 °C 14.1: NaOMe / methanol / 4 h / 20 °C 15.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 16.1: K2CO3 / acetone / 2 h / 20 °C | ||
Multi-step reaction with 18 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: aq. AcOH / 12 h / 70 °C 15.1: pyridine / 5 h / 50 °C 16.1: NaOMe / methanol / 4 h / 20 °C 17.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 18.1: K2CO3 / acetone / 2 h / 20 °C |
Multi-step reaction with 17 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: K2CO3 / acetone / 2 h / 20 °C | ||
Multi-step reaction with 18 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 65 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: 98 percent / aq. AcOH 15.1: pyridine / 5 h / 50 °C 16.1: 169 mg / sodium methoxide; methanol / 4 h / 20 °C 17.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 18.1: K2CO3 / acetone / 2 h / 20 °C | ||
Multi-step reaction with 17 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 32 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 98 percent / aq. AcOH 14.1: pyridine / 5 h / 50 °C 15.1: 169 mg / sodium methoxide; methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: K2CO3 / acetone / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 15 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 12.1: 80 percent / pyridine / 12 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C | ||
Multi-step reaction with 14 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 12.1: aq. AcOH / 12 h / 70 °C 13.1: pyridine / 5 h / 50 °C 14.1: NaOMe / methanol / 4 h / 20 °C | ||
Multi-step reaction with 16 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: aq. AcOH / 12 h / 70 °C 15.1: pyridine / 5 h / 50 °C 16.1: NaOMe / methanol / 4 h / 20 °C |
Multi-step reaction with 15 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C | ||
Multi-step reaction with 16 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 65 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: 98 percent / aq. AcOH 15.1: pyridine / 5 h / 50 °C 16.1: 169 mg / sodium methoxide; methanol / 4 h / 20 °C | ||
Multi-step reaction with 15 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 32 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 98 percent / aq. AcOH 14.1: pyridine / 5 h / 50 °C 15.1: 169 mg / sodium methoxide; methanol / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 14 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 70 percent / Et3N / ethanol / 24 h / 20 °C 12.1: aq. AcOH / 12 h / 70 °C 13.1: pyridine / 5 h / 50 °C 14.1: NaOMe / methanol / 4 h / 20 °C | ||
Multi-step reaction with 15 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 70 percent / Et3N / ethanol / 24 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C | ||
Multi-step reaction with 16 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 20 percent / tetrahydrofuran / 24 h / 20 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: 98 percent / aq. AcOH 15.1: pyridine / 5 h / 50 °C 16.1: 134 mg / sodium methoxide; methanol / 4 h / 20 °C |
Multi-step reaction with 15 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 70 percent / tetrahydrofuran / 24 h / 20 °C 13.1: 98 percent / aq. AcOH 14.1: pyridine / 5 h / 50 °C 15.1: 134 mg / sodium methoxide; methanol / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 18 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 12.1: 80 percent / pyridine / 12 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: K2CO3 / acetone / 2 h / 20 °C 18.1: 80 mg / tetrahydrofuran / 24 h / 20 °C | ||
Multi-step reaction with 17 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 12.1: aq. AcOH / 12 h / 70 °C 13.1: pyridine / 5 h / 50 °C 14.1: NaOMe / methanol / 4 h / 20 °C 15.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 16.1: K2CO3 / acetone / 2 h / 20 °C 17.1: 80 mg / tetrahydrofuran / 24 h / 20 °C | ||
Multi-step reaction with 19 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: aq. AcOH / 12 h / 70 °C 15.1: pyridine / 5 h / 50 °C 16.1: NaOMe / methanol / 4 h / 20 °C 17.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 18.1: K2CO3 / acetone / 2 h / 20 °C 19.1: 80 mg / tetrahydrofuran / 24 h / 20 °C |
Multi-step reaction with 18 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: K2CO3 / acetone / 2 h / 20 °C 18.1: 80 mg / tetrahydrofuran / 24 h / 20 °C | ||
Multi-step reaction with 19 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 65 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: 98 percent / aq. AcOH 15.1: pyridine / 5 h / 50 °C 16.1: 169 mg / sodium methoxide; methanol / 4 h / 20 °C 17.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 18.1: K2CO3 / acetone / 2 h / 20 °C 19.1: 80 mg / tetrahydrofuran / 24 h / 20 °C | ||
Multi-step reaction with 18 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 32 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 98 percent / aq. AcOH 14.1: pyridine / 5 h / 50 °C 15.1: 169 mg / sodium methoxide; methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: K2CO3 / acetone / 2 h / 20 °C 18.1: 80 mg / tetrahydrofuran / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 16 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 12.1: 80 percent / pyridine / 12 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C | ||
Multi-step reaction with 15 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 12.1: aq. AcOH / 12 h / 70 °C 13.1: pyridine / 5 h / 50 °C 14.1: NaOMe / methanol / 4 h / 20 °C 15.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C | ||
Multi-step reaction with 17 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: aq. AcOH / 12 h / 70 °C 15.1: pyridine / 5 h / 50 °C 16.1: NaOMe / methanol / 4 h / 20 °C 17.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C |
Multi-step reaction with 16 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C | ||
Multi-step reaction with 17 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 65 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: 98 percent / aq. AcOH 15.1: pyridine / 5 h / 50 °C 16.1: 169 mg / sodium methoxide; methanol / 4 h / 20 °C 17.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C | ||
Multi-step reaction with 16 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 32 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 98 percent / aq. AcOH 14.1: pyridine / 5 h / 50 °C 15.1: 169 mg / sodium methoxide; methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 15 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 70 percent / Et3N / ethanol / 24 h / 20 °C 12.1: aq. AcOH / 12 h / 70 °C 13.1: pyridine / 5 h / 50 °C 14.1: NaOMe / methanol / 4 h / 20 °C 15.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C | ||
Multi-step reaction with 16 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 70 percent / Et3N / ethanol / 24 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C | ||
Multi-step reaction with 17 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 20 percent / tetrahydrofuran / 24 h / 20 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: 98 percent / aq. AcOH 15.1: pyridine / 5 h / 50 °C 16.1: 134 mg / sodium methoxide; methanol / 4 h / 20 °C 17.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C |
Multi-step reaction with 16 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 70 percent / tetrahydrofuran / 24 h / 20 °C 13.1: 98 percent / aq. AcOH 14.1: pyridine / 5 h / 50 °C 15.1: 134 mg / sodium methoxide; methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 90 percent / Et3N / ethanol / 24 h / 20 °C 12.1: aq. AcOH / 12 h / 70 °C | ||
Multi-step reaction with 13 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 90 percent / Et3N / ethanol / 24 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C | ||
Multi-step reaction with 13 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 90 percent / Et3N / ethanol / 72 h / 20 °C 13.1: 99 percent / aq. AcOH / 12 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 16 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 70 percent / Et3N / ethanol / 24 h / 20 °C 12.1: aq. AcOH / 12 h / 70 °C 13.1: pyridine / 5 h / 50 °C 14.1: NaOMe / methanol / 4 h / 20 °C 15.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 16.1: N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide; 1-hydroxybenzotriazole; N,N-diisopropylethylamine / CH2Cl2 / 12 h / 20 °C | ||
Multi-step reaction with 17 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 70 percent / Et3N / ethanol / 24 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C 15.1: NaOMe / methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide; 1-hydroxybenzotriazole; N,N-diisopropylethylamine / CH2Cl2 / 12 h / 20 °C | ||
Multi-step reaction with 19 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 20 percent / tetrahydrofuran / 24 h / 20 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: 98 percent / aq. AcOH 15.1: pyridine / 5 h / 50 °C 16.1: 134 mg / sodium methoxide; methanol / 4 h / 20 °C 17.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 18.1: K2CO3 / acetone / 2 h / 20 °C 19.1: 48 mg / tetrahydrofuran / 24 h / 20 °C |
Multi-step reaction with 18 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 70 percent / tetrahydrofuran / 24 h / 20 °C 13.1: 98 percent / aq. AcOH 14.1: pyridine / 5 h / 50 °C 15.1: 134 mg / sodium methoxide; methanol / 4 h / 20 °C 16.1: pyridinium dichromate / dimethylformamide / 20 h / 20 °C 17.1: K2CO3 / acetone / 2 h / 20 °C 18.1: 48 mg / tetrahydrofuran / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 14 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 12.1: 80 percent / pyridine / 12 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C | ||
Multi-step reaction with 13 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 12.1: aq. AcOH / 12 h / 70 °C 13.1: pyridine / 5 h / 50 °C | ||
Multi-step reaction with 15 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 65 percent / NH3 / ethanol / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: aq. AcOH / 12 h / 70 °C 15.1: pyridine / 5 h / 50 °C |
Multi-step reaction with 14 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 32 percent / NH3 / ethanol / 24 h / 50 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C | ||
Multi-step reaction with 15 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 65 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: 98 percent / aq. AcOH 15.1: pyridine / 5 h / 50 °C | ||
Multi-step reaction with 14 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 32 percent / ethanolic NH3 / 24 h / 50 °C 13.1: 98 percent / aq. AcOH 14.1: pyridine / 5 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 13 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 10.2: 54 percent / acetonitrile; 1,2-dichloro-ethane / 24 h / 83 °C 11.1: 70 percent / Et3N / ethanol / 24 h / 20 °C 12.1: aq. AcOH / 12 h / 70 °C 13.1: pyridine / 5 h / 50 °C | ||
Multi-step reaction with 14 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / LiAlH4 / tetrahydrofuran / 5 h / 20 °C 3.1: 98 percent / pyridine / 4 h / 0 °C 4.1: 94 percent / Na2S*H2O / dimethylformamide / 3 h / 100 °C 5.1: 43 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: Et3N; TMSOTf / acetonitrile; 1,2-dichloro-ethane / 20 °C 11.2: acetonitrile; 1,2-dichloro-ethane / 20 - 80 °C 12.1: 70 percent / Et3N / ethanol / 24 h / 20 °C 13.1: aq. AcOH / 12 h / 70 °C 14.1: pyridine / 5 h / 50 °C | ||
Multi-step reaction with 15 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 20 percent / tetrahydrofuran / 24 h / 20 °C 13.1: 80 percent / pyridine / 12 h / 20 °C 14.1: 98 percent / aq. AcOH 15.1: pyridine / 5 h / 50 °C |
Multi-step reaction with 14 steps 1.1: CuSO4; H2SO4 / 24 h / 20 °C 2.1: 24.1 g / NaBH4 / methanol / 2 h / 20 °C 3.1: 98 percent / pyridine / CH2Cl2 / 5 h / 5 °C 4.1: 94 percent / Na2S / dimethylformamide / 3 h / 100 °C 5.1: 42 percent / aq. AcOH / 4 h / 20 °C 6.1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.17 h 7.1: 98 percent / NaBH4 / methanol / 0.5 h / 0 °C 8.1: 99 percent / pyridine / 6 h / 20 °C 9.1: 95 percent / m-CPBA / CH2Cl2 / 0.75 h / -78 °C 10.1: 62 percent / 6 h / 100 °C 11.1: HMDS; ammonium sulfate / 6 h / Heating 11.2: 58.5 percent / TMSOTf / 1,2-dichloro-ethane / 8 h / Heating 12.1: 70 percent / tetrahydrofuran / 24 h / 20 °C 13.1: 98 percent / aq. AcOH 14.1: pyridine / 5 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: TsOH / benzene / 10 h / Heating 2: DIBAL / tetrahydrofuran; toluene / 1 h / -78 °C | ||
Multi-step reaction with 2 steps 1: 97 percent / p-toluenesulfonic acid, molecular sieves (4A) / benzene / 10 h / Heating 2: 88 percent / 1 M DIBAL / toluene; tetrahydrofuran / 1 h / -78 °C | ||
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / 110 °C 2: diisobutylaluminium hydride / toluene; tetrahydrofuran / -5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: TsOH / benzene / 10 h / Heating 2: DIBAL / tetrahydrofuran; toluene / 1 h / -78 °C 3: NH2OH*HCl, py / 2 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: 97 percent / p-toluenesulfonic acid, molecular sieves (4A) / benzene / 10 h / Heating 2: 88 percent / 1 M DIBAL / toluene; tetrahydrofuran / 1 h / -78 °C 3: 96 percent / hydroxylamine hydrochloride / pyridine / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: TsOH / benzene / 10 h / Heating 2: DIBAL / tetrahydrofuran; toluene / 1 h / -78 °C 3: NH2OH*HCl, py / 2 h / Ambient temperature 4: toluene, reflux, 14 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With toluene-4-sulfonic acid In toluene for 19h; Heating / reflux; | 5 ER-812772 (1wt, 1 eq) was dissolved in ethyl acetate (8 v). 10% Palladium on carbon (0.05 wt, 0.01 eq) was added, the reaction purged with nitrogen then stirred under hydrogen atmosphere for 2 hours. The catalyst was removed by filtration through Celite with ethyl acetate washed. The combined filtrates were concentrated in vacuo to afford ER- 812829 as a white solid. Example 5 Preparation of F-3a: [00173] D-Gulonolactone (1 wt. , 1 eq. ), cyclohexanone (2 to 3 eq. ), toluene (6 vol. ), and p-toluenesulfonic acid (0.021 wt., 0.02 eq. ) were charged to the reaction vessel. Reaction mixture was heated to reflux with stirring. Upon azeotropic removal of water the reaction was complete. The reaction mixture was cooled to 85 to 90°C and agitation was increased. Heptane (5.2 vol. ) was added over 20-30 minutes with stirring. Cooled to 65-70°C and stirred for 30 minutes at 65-70°C. The solid product was filtered at 65-70°C, maintaining mother liquor temp > 35 °C. Re-filtered at 35-40°C and maintained the mother liquor at ambient temperature for 30 minutes. Re-filtered the mother liquor. The filter cake was washed two times with heptane (2 x 1.7 vol. ) then dried to afford ER-805715. Yield 84% (1.6 wt.). [00174] In an alternate method for preparing ER-805715, D-gulonolactone (1 wt), cyclohexanone (1.32 wt, 2.4 eq), p-TsOH-monohydrate (0.02 wt, 0.02 eq) and toluene (12 vol) were refluxed together for 19 hours, while azeotropically removing water. The mixture was washed with 5% aqueous NaHC03 (4 vol) followed by saturated aqueous NaCI (2 vol x 2, pH=7). The organic phase was concentrated by distillation (ca. 4.5 vol of toluene remaining) and cooled to 100 °C before heptane (10 vol) was added, maintaining internal temperature > 80 °C. The mixture was heated to reflux for at least 1 hour before it was cooled to and aged at 85 °C for 3 hours, at 80 °C for 3 hrs and then cooled to 40 °C in 12 hrs. The product was collected by filtration and the cake washed with heptane (2 vol). The filter cake was dried by airflow to afford ER-805715 (1.48 wt) in 78% of yield. |
60% | With toluene-4-sulfonic acid In toluene at 110℃; | |
95 %Chromat. | With pyridinium p-toluenesulfonate In toluene for 22h; Dean-Stark apparatus; Reflux; | 5.2 Example 5-2; Synthesis of compound (8) from D-gulonic γ-lactone; 540 g of toluene was added to 90 g of D-gulonic γ-lactone and 101.70 g of cyclohexanone. 3.81 g of p-toluenesulfonic acid-pyridine complex was added at room temperature. A Dean-Stark device was attached, followed by agitation under reflux under dehydrating conditions for 22 hours. The solution was cooled to 40° C., to which 360 g of tetrahydrofuran was added. The determination of a content of compound (9) in the solution revealed that the amount was at 162.21 g and the yield was at 95%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With hydrogenchloride In water at 20℃; | 11 3.5-0-Benzvlidene-D-qulonolactone2.2; D-gulonolactone 2.1 (25.0 g, 140 mmol) was suspended in benzaldehyde (200 ml) and 37% hydrochloric acid (15 ml) was added. The resulting mixture was stirred overnight at room temperature. Diethyl ether (200 ml) was then added and the crystal mass was filtered. After washing the crystals with copious diethyl ether and drying in vacuo, the product (25.1 g, 67%) was obtained as white crystals.[a]D -58.2 (c 0.79, DMF) {Lit. [a]D +61.1 (DMF) for the enantiomeric]; m.p. 188 °C {Lit. 188-189 °C for the enantiomer}; 5H (400 MHz, cf-DMSO) 3.60 (2H, d, H-6a, H-6b, J 6.6 Hz), 4.16 (1H, app. t, H-5, J 6.6 Hz), 4.34(1H, s, H-4), 4.70 (2H, s, H-2, H-3), 5.71 (1H, s, Ar-CH), 7.37 (3H, m, ArH), 7.43 (2H, m, ArH); 5H (100 MHz, d6-DMSO) 60.5 (C-6), 70.1 (C-4), 71.4, 75.6 (C-2, C-3), 76.9 (C-5), 98.9 (Ar-CH), 127.3, 128.8, 129.7, 138.6 (ArC), 176.7 (C=0). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone | 1.A A. A. 2,3:5,6-Di-O-isopropylidene-D-gulono-γ-lactone D-Gulono-γ-lactone (15.47 g, 86.9 mmol) was stirred with acetone (160 ml), 2,2 dimethoxypropane (40 ml) and a catalytic amount of para-toluene-sulphonic acid under dry nitrogen for 36 hr when thin layer chromatography (t.l.c.) (ethyl acetate) revealed no starting material Rf 0.0 and one product Rf 0.9. The reaction mixture was stirred with an excess of sodium bicarbonate and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane (200 ml) and washed with water (3*200 ml). The organic extracts were dried (MgSO4) and the solvent removed under reduced pressure to give a white crystalline solid which was recrystallized from ethyl acetate to yield the title compound (18.38 g, 82%) as a white crystalline solid. M.p. 151°-153° C. (lit 152°-153° C.). [α]D20 -70° (c 1 in acetone) (lit. -64° (c 2.8 in acetone)). 13 C NMR (CDCl3); 173.3 (s, C-1), 114.7 (s), 110.5 (s), 80.9, 76.0, 75.7 and 75.2 (4*d, C-2, C-3, C-4 and C-5), 65.1 (d, C-6), 26.5 (q), 25.7 (q), 25.0 (q). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: acetone; D-gulono-1,4-lactone With sulfuric acid; copper(II) sulfate at 20℃; for 24h; Stage #2: With diisobutylaluminium hydride In tetrahydrofuran; toluene at -78℃; for 1h; | 19 (3aR,4R,6S,6aR)-6-((R)-2,2-dimethyl-1,3-dioxolane)-2,2-dimethyltetrahydrofuran[3,4-d][1,3]dioxole-4-ol (62) After dissolving the compound D-gulonic acid lactone (20.01 g, 112.37 mmol) and anhydrous copper sulfate (25.0 g, 157.22 mmol) in dry acetone (450 mL), concentrated sulfuric acid (1.6 mL) was added, The solution was stirred at room temperature for 24 hours. It is not necessary to adjust the reaction solution to pH 7 with calcium hydroxide, filter the suspension, concentrate the mother liquor to obtain a pale yellow syrupy diacetone, and purify it as it is for the next reaction step It was possible. The obtained diacetone was dissolved in THF (300 mL) and cooled to -78 ° C. Then, a 1 M solution of DIBAL-H in toluene (180 mL, 180 mM) was slowly dropped, and the reaction mixture was cooled to -78 ° C. For 1 hour. After removing the reaction solution with water (50 mL), filtration was carried out, the organic layer was separated, dried with anhydrous sodium sulfate, and concentrated by filtration. Separation by silica gel column chromatography (n-hexane / ethyl acetate = 5: 1) gave the desired compound as a colorless morphology syrup (25.27 mmol, total yield of 83%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; copper(II) sulfate at 20℃; for 24h; | 19 Example 19. (3aR,4R,65,6aR)-6-((R)-2,2-dimethyl-,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-furo[3,4-d][1,3]dioxol-4-ol (62) To a stirred slurry of D-gulonic-lactone (20.01 g,112.37 mmol) and anhydrous Cu504 (25.0 g, 157.22 mmol)dry acetone (450 mE) was added conc. H2504 (1.6 mE), and the mixture was stirred for 24 h at room temperature. The pH of the solution was adjusted to 7 with Ca(OH)2, and the resulting slurry was filtered and evaporated in vacuo to afford a diacetonide (2,3: 5,6-O-diisopropylidene-D-gulono-,4-lactone) as a light-yellow syrup which was used in the next step without thrther purification. To a stirred solution of diacetonide in THF (300 mE) at -78° C. was added slowly 1 M solution of DII3AE-H (180 ml, 180 mM) in toluene. After being stirred for 1 h at -78° C., the reaction mixture was quenched with water (50 mE) and filtered through Celite. The organic layer was separated, dried (Na2SO4,), and concentrated in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: acetone; D-gulono-1,4-lactone With sulfuric acid; copper(II) sulfate at 20℃; for 24h; Stage #2: With diisobutylaluminium hydride In tetrahydrofuran; toluene at -78℃; for 1h; | 19 Example 19. (3aR, 4R, 6S, 6aR) -6-((R) -2,2-dimethyl-1,3-dioxolane) -2,2-dimethyltetrahydrofuran [3,4 -d] [1,3] diox-4-ol (62) Compound D-gulonic acid lactone (20.01 g, 112.37 mmol) and anhydrous copper sulfate (25.0 g, 157.22 mmol) were dissolved in dry acetone (450 mL), then concentrated sulfuric acid (1.6 mL) was added, and the reaction was mixed. The solution was stirred at room temperature for 24 h.The reaction solution was adjusted to pH 7 with calcium hydroxide, the suspension was filtered, and the mother liquor was concentrated to obtain a pale yellow syrupy diacetone compound, which can be directly used in the next reaction without purification.The diacetone compound obtained above was dissolved in THF (300 mL), cooled to -78 ° C, and then a 1M solution of DIBAL-H in toluene (180 mL, 180 mM) was slowly added dropwise, and the reaction mixture was stirred at -78 ° C for 1 h.The reaction solution was quenched with water (50 mL), filtered, and the organic layer was separated, dried over anhydrous sodium sulfate, filtered, and concentrated.Separation on a silica gel column (n-hexane / ethyl acetate = 5: 1) gave the title compound (25.27 mmol, 83% in two steps) as a colorless syrup. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In ethanol; butan-1-ol Reflux; | 3.2. 2-(D-gulo-pentitol-1-yl)benzimidazole analogs General procedure: Generally, a mixture of D-gulonic acid-γ-lactone (1 mol), o-phenylenediaminedihydrochloride derivatives (1.1 mol), ethanol (10 mL)and n-butanol (15 mL) was refluxed for 6-8 h. The product obtainedwas cooled and evaporated till dryness. The syrupy product was dissolvedin water about (15 mL), neutralized with dilute ammonia solution.It gave a precipitate which was filtered, washed with acetone anddried. The product was recrystallized from ethanol giving colorlessneedles, for 1H NMR data see Table 1.3.2.1. 2-(D-gulo-pentitol-1-yl)benzimidazole 1It was prepared by condensation of D-gulonic acid-γ-lactone (1.0 g)and o-phenylenediamine dihydrochloride (1.01 g); yield 0.90 g (60%),m.p. 195-196 °C, Rf 0.58 (solvent A), [ ]D25 +12.8 (c 1.01, 0.1 N HCl).Anal. Calcd for C12H16N2O5: C, 53.72; H, 6.011; N, 10.44%. Found: C,53.92; H, 6.12; N, 10.50%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In ethanol; butan-1-ol Reflux; | 3.2. 2-(D-gulo-pentitol-1-yl)benzimidazole analogs General procedure: Generally, a mixture of D-gulonic acid-γ-lactone (1 mol), o-phenylenediaminedihydrochloride derivatives (1.1 mol), ethanol (10 mL)and n-butanol (15 mL) was refluxed for 6-8 h. The product obtainedwas cooled and evaporated till dryness. The syrupy product was dissolvedin water about (15 mL), neutralized with dilute ammonia solution.It gave a precipitate which was filtered, washed with acetone anddried. The product was recrystallized from ethanol giving colorlessneedles, for 1H NMR data see Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.4% | In ethanol; butan-1-ol Reflux; | 3.2. 2-(D-gulo-pentitol-1-yl)benzimidazole analogs General procedure: Generally, a mixture of D-gulonic acid-γ-lactone (1 mol), o-phenylenediaminedihydrochloride derivatives (1.1 mol), ethanol (10 mL)and n-butanol (15 mL) was refluxed for 6-8 h. The product obtainedwas cooled and evaporated till dryness. The syrupy product was dissolvedin water about (15 mL), neutralized with dilute ammonia solution.It gave a precipitate which was filtered, washed with acetone anddried. The product was recrystallized from ethanol giving colorlessneedles, for 1H NMR data see Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.2% | In ethanol; butan-1-ol Reflux; | 3.2. 2-(D-gulo-pentitol-1-yl)benzimidazole analogs General procedure: Generally, a mixture of D-gulonic acid-γ-lactone (1 mol), o-phenylenediaminedihydrochloride derivatives (1.1 mol), ethanol (10 mL)and n-butanol (15 mL) was refluxed for 6-8 h. The product obtainedwas cooled and evaporated till dryness. The syrupy product was dissolvedin water about (15 mL), neutralized with dilute ammonia solution.It gave a precipitate which was filtered, washed with acetone anddried. The product was recrystallized from ethanol giving colorlessneedles, for 1H NMR data see Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.33% | In ethanol; butan-1-ol Reflux; | 3.2. 2-(D-gulo-pentitol-1-yl)benzimidazole analogs General procedure: Generally, a mixture of D-gulonic acid-γ-lactone (1 mol), o-phenylenediaminedihydrochloride derivatives (1.1 mol), ethanol (10 mL)and n-butanol (15 mL) was refluxed for 6-8 h. The product obtainedwas cooled and evaporated till dryness. The syrupy product was dissolvedin water about (15 mL), neutralized with dilute ammonia solution.It gave a precipitate which was filtered, washed with acetone anddried. The product was recrystallized from ethanol giving colorlessneedles, for 1H NMR data see Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In ethanol; butan-1-ol Reflux; | 3.2. 2-(D-gulo-pentitol-1-yl)benzimidazole analogs General procedure: Generally, a mixture of D-gulonic acid-γ-lactone (1 mol), o-phenylenediaminedihydrochloride derivatives (1.1 mol), ethanol (10 mL)and n-butanol (15 mL) was refluxed for 6-8 h. The product obtainedwas cooled and evaporated till dryness. The syrupy product was dissolvedin water about (15 mL), neutralized with dilute ammonia solution.It gave a precipitate which was filtered, washed with acetone anddried. The product was recrystallized from ethanol giving colorlessneedles, for 1H NMR data see Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.9% | In ethanol; butan-1-ol Reflux; | 3.2. 2-(D-gulo-pentitol-1-yl)benzimidazole analogs General procedure: Generally, a mixture of D-gulonic acid-γ-lactone (1 mol), o-phenylenediaminedihydrochloride derivatives (1.1 mol), ethanol (10 mL)and n-butanol (15 mL) was refluxed for 6-8 h. The product obtainedwas cooled and evaporated till dryness. The syrupy product was dissolvedin water about (15 mL), neutralized with dilute ammonia solution.It gave a precipitate which was filtered, washed with acetone anddried. The product was recrystallized from ethanol giving colorlessneedles, for 1H NMR data see Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35.8 g | With zinc(II) chloride In toluene for 10h; Reflux; | 1 Preparation of Compound I: 20.0 g of D-gulonic acid lactone, 31.5 g of p-methylcyclohexanone, 100 ml of toluene, and 0.31 g of anhydrous zinc chloride were stirred and refluxed for reaction for 10 hours while removing water through an oil-water separator. After the reaction mixture was cooled, it was washed successively with 50 ml of sodium bicarbonate aqueous solution and 50 ml of saturated sodium chloride aqueous solution. After the organic phase was concentrated to remove part of the toluene, 200ml of n-heptane was added, heated to reflux for 2 hours, cooled to 40°C and stirred for 2 hours. It was filtered and dried to obtain 35.8 g of compound I. |
Tags: 6322-07-2 synthesis path| 6322-07-2 SDS| 6322-07-2 COA| 6322-07-2 purity| 6322-07-2 application| 6322-07-2 NMR| 6322-07-2 COA| 6322-07-2 structure
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