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CAS No. : | 14686-89-6 | MDL No. : | MFCD00069693 |
Formula : | C12H20O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 260.28 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 60.12 |
TPSA : | 66.38 Ų |
GI absorption : | High |
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) : | -7.9 cm/s |
Log Po/w (iLOGP) : | 2.73 |
Log Po/w (XLOGP3) : | -0.02 |
Log Po/w (WLOGP) : | 0.38 |
Log Po/w (MLOGP) : | -0.06 |
Log Po/w (SILICOS-IT) : | 0.65 |
Consensus Log Po/w : | 0.73 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.38 |
Solubility : | 11.0 mg/ml ; 0.0422 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.92 |
Solubility : | 31.0 mg/ml ; 0.119 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.6 |
Solubility : | 66.0 mg/ml ; 0.254 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 4.57 |
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 |
---|---|---|
68% | With magnesium; ethylene dibromide In diethyl ether at -30℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With tetra-n-butylammonium cyanide; triphenylphosphine; methyl trifluoromethanesulfonate In toluene at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With hydrogenchloride In acetone at 60℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With pyridine In dichloromethane at -20℃; for 0.5h; | |
90% | With pyridine In dichloromethane at -20℃; for 2h; | |
83% | With pyridine In dichloromethane at -78 - 0℃; |
With pyridine In dichloromethane at -30℃; for 0.5h; | ||
With pyridine In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triethylamine In dichloromethane for 0.166667h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With acetic acid In water for 16h; Ambient temperature; | |
70% | With iodine In methanol for 4.5h; Heating; | |
With acetic acid for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With pyridine; diethylamino-sulfur trifluoride In dichloromethane | |
71.5% | With pyridine; diethylamino-sulfur trifluoride In dichloromethane for 15h; Ambient temperature; | |
64% | With dmap; diethylamino-sulfur trifluoride In dichloromethane 1) -20 deg C, 15 min, 2) RT, 24 h; |
53% | With diethylamino-sulfur trifluoride | |
Multi-step reaction with 2 steps 1: 90 percent / pyridine / CH2Cl2 / 2 h / -20 °C 2: 43 percent / cesium fluoride / DMF, reflux, 30 min then petroleum ether, reflux, 15 min | ||
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 2: tris(dimethylamino)sulfonium difluorotrimethylsilicate / CH2Cl2 / 0.17 h / 0 - 20 °C | ||
Multi-step reaction with 2 steps 1: pyridine 2: potassium fluoride / various solvent(s) / 200 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium tetrahydroborate In ethanol; water | |
85% | With sodium tetrahydroborate In tetrahydrofuran | |
81% | With sodium tetrahydroborate In methanol |
With sodium tetrahydroborate In ethanol; water at 2℃; for 1.5h; Yield given; | ||
With sodium tetrahydroborate | ||
With sodium tetrahydroborate | ||
With sodium tetrahydroborate In ethanol at 2℃; for 1.5h; | ||
1.35 g | With sodium tetrahydroborate In ethanol; water | |
With sodium tetrahydroborate In ethanol; water for 5h; Ambient temperature; Yield given; | ||
With sodium tetrahydroborate In ethanol Yield given; | ||
With sodium tetrahydroborate Yield given; | ||
With sodium tetrahydroborate; ethanol; water at -20 - 0℃; for 0.5h; | ||
With sodium tetrahydroborate In ethanol; water for 3h; Ambient temperature; Yield given; | ||
With sodium tetrahydroborate In ethanol; water at 0℃; for 1h; Yield given; | ||
With sodium tetrahydroborate In ethanol | ||
With sodium tetrahydroborate; acetic anhydride 1.) pyridine, reflux, 2.) EtOH; Multistep reaction; | ||
Multi-step reaction with 3 steps 1: 90 percent / pyridine / 10 h / Heating 2: 98 percent / H2 / Pd-C / ethyl acetate / 20 h / 20 °C / 1810.02 Torr 3: 99 percent / H2O; triethylamine / methanol / 3 h / 20 °C | ||
Multi-step reaction with 3 steps 1: pyridine 2: H2 / Pd black / ethyl acetate 3: K2CO3 / methanol | ||
Multi-step reaction with 3 steps 1.1: diethyl ether; water / 7 h / Reflux 1.2: 75 °C 2.1: palladium on activated charcoal; hydrogen / methanol / 120 h / 20 °C 3.1: sodium methylate / methanol / 3 h / 20 °C / pH 9.5 | ||
Stage #1: 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose With pyridine; acetic anhydride Inert atmosphere; Stage #2: With palladium on activated charcoal; hydrogen Inert atmosphere; Stage #3: With sodium hydroxide Inert atmosphere; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With base In methanol Irradiation; | |
65% | With hydrazine In water; acetonitrile for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane for 15h; Ambient temperature; | ||
With pyridine | ||
With pyridine In dichloromethane at -10℃; for 1h; |
With pyridine In dichloromethane at -20℃; for 0.5h; | 9.5-9.6 Step~5 and 6 : (3aR,5R,6S,6aR)-6-azido-5-((R)-2,2-dimethyl-1 ,3-dioxolan-4~yl)-2,2- dimethyi tetrahydrofuro[2,3-d][1 ,3]dioxole: [00272] To a stirred solution of SaR.SR^R.eaRJ-S-^R^^-dimetbyl- S- dioxoian-4-yi)-2,2-dimethyltetra hydrofuro[2,3-d][1 ,3]dioxo-6-o (510 g) in DC :pyridine (3.0 eq) was slowly added triflic anhydride in DCM at -20 °C and the reaction mixture was stirred at same temperature for 30 min. after completion, the reaction mixture was quenched with ice cold 1 N HCi (pH ~ 8) and the aqueous layer was extracted with DCM (2 x 1000 mL), dried (Na2S04) and concentrated. This crude residue was dissolved in DMF and NaN3 (5.0 eq) was added portionwise at 0 °C and stirred at the same temperature for 3 h. After completion, the reaction mixture was poured into ice water (500 mL) and extracted with ethyl acetate (2 x 1000 mL). The combined organic layer was again washed with ice cold water (3 x 500 mL), dried (Na2S04) and concentrated. The residue was purified by flash column chromatography [normal phase, silica gel (100-200 mesh), gradient 0 to 5% EtOAc in hexane] to afford the title compound as pale yellow gum (150 g, 27%). 1 H N R (400 MHz, CDCI3): L 5.80 (d, J = 3.8 Hz, 1 H), 4.60 - 4.63 (m, 1 H) 4.35 - 4.39 (m, 1 H), 4.10 (t, J = 3.6 Hz, 1 H), 3.94 (d, J = 2.8 Hz, 1 H), 3.89 - 3.93 (m, 2H), 1 .58 (s, 3H), 1 .55 (s, 3H), 1 .45 (s, 3H), 1 .36 (s, 3H). | |
With pyridine In tert-butyl methyl ether at 5 - 10℃; for 3h; | Alternative process To a solution of l,2:5,6-di-0-isopropylidene-a-D-gulofuranose, VI (200 g, 0.77 mol) in TBME (540 mL) pyridine (112 mL, 1.84 mol) was added and the solution cooled to 5 °C. Trifluoromethanesulfonic anhydride (262 g, 0.93 mol) was added over 2 hours to the suspension maintaining 5 °C followed by TBME (72 mL). The reaction mixture was warmed to 10 °C and stirred for 1 hour then quenched by addition of sodium bisulphite solution [made from pre-mixed 50% aqueous NaOH (22.0 g), water (138 mL) and 95% sulphuric acid (56 g)] at 5 °C. Water (140 mL) was added and the mixture warmed to 20 °C. The layers were separated and the organic phase washed with water (140 mL), 5% aqueous NaHCCb solution (140 mL) then 18% aqueous NaCl solution (128 mL) at 20 °C. The layers were separated and triethylamine hydrochloride (80 g, 0.58 mol) and tetrabutyl ammonium bromide (TBAB) (24.0 g, 0.16 mol) added to the organic phase. Sodium azide (74 g, 1.14 mol) dissolved in water (200 mL) was added at 20 °C then the mixture heated to 50 °C. The reaction was held for 20 hours then cooled to 20 °C and water (400 mL) added. The phases were separated and the organic phase washed with water (200 mL) then 18% aqueous sodium chloride (120 mL). A solvent exchange to 2-methyl tetrahydrofuran (2-MeTHF)was performed through distillation in vacuo at up to 60°C. 3-azido-3-deoxy-l,2:5,6-di-0-isopropylidene-a-D-galactofuranose VIII (206 g, 94% th over two steps from VI) was progressed to the manufacture of l,2,4,6-Tetra-0-acetyl-3- azido-3-deoxy-P-D-galactopyranose X, as a solution in 2-MeTHF, ca. 840 mL total volume. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.3% | With dmap; diethylamino-sulfur trifluoride In dichloromethane for 24h; Ambient temperature; | |
84% | With dmap; diethylamino-sulfur trifluoride In dichloromethane at -10 - 20℃; for 48h; | |
63% | With dmap; diethylamino-sulfur trifluoride In dichloromethane at 20℃; for 24h; Inert atmosphere; Cooling; |
With diethylamino-sulfur trifluoride | ||
With 4,4'-diaminostilbene-2,2'-disulfonic acid | ||
Multi-step reaction with 2 steps 1: 92 percent / pyridine / 60 °C 2: 1) dehydrated Amberlyst-A-26 (F(-)) resin; 2) H2, NaHCO3 / 2) 5percent Pd-on-charcoal / 1) benzene, reflux; 2) EtOH, 1 Atm, room temp., 30 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: (1,2:5,6)-di-O-isopropylidene-D-gulose With pyridine; trifluoromethylsulfonic anhydride In dichloromethane for 0.5h; Cooling with ice; Stage #2: With trimethylsilylazide; sodium fluoride In N,N-dimethyl-formamide at 50℃; | 3-5 Example 3 General procedure: Compound I (29.9g, 114.88mmol) was dissolved in dichloromethane (100mL), pyridine (27.81mL, 344.6mmol) was added, after cooling to the ice bath temperature, trifluoromethanesulfonic anhydride (38.6mL, 229.7mmol) was added dropwise, After stirring for 30 min under ice bath, TLC (PE:EA=1:1) showed that the reaction was complete. The reaction solution was washed with 1N HCla.q., sat.NaHCO3a.q. and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The brown syrup intermediate is obtained, which is directly used in the next reaction;Azidotrimethylsilane (52.9mL, 402.1mmol) and sodium fluoride (15.9g, 379.1mmol) were mixed in DMF (150mL), refluxed in an oil bath at 100°C for 1 hour, cooled to room temperature, and added The DMF solution of the brown syrup intermediate obtained in the step reaction, the mixture was refluxed overnight in an oil bath at 50°C, TLC (PE:EA=1:1) detected that the reaction was complete, the reaction solution was cooled to room temperature, poured into water, and the mixture was subjected to dichloromethane Methane extraction three times (3*300mL), combine the organic phases, wash with brine, dry with anhydrous sodium sulfate, concentrate and mix the sample, separate by column chromatography (PE:EA=6:1) to obtain colorless syrup II, which will solidify after standing for a long time (29.64g, 90.2%). |
73% | With tris-(2-chloro-ethyl)-amine; thiamine diphosphate; diethylazodicarboxylate In benzene at 60℃; for 0.5h; | |
Multi-step reaction with 2 steps 1: pyridine 2: NaN3 / dimethylformamide |
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / 15 h / Ambient temperature 2: sodium azide / dimethylformamide / 2 h | ||
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 0.5 h / -20 °C 2: sodium azide / N,N-dimethyl-formamide / 3 h / 0 °C | ||
Multi-step reaction with 2 steps 1: pyridine / tert-butyl methyl ether / 3 h / 5 - 10 °C 2: sodium azide; triethylamine hydrochloride; tetrabutylammomium bromide / tert-butyl methyl ether; water / 20 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With methanol; sodium methylate for 2h; | |
99% | With water; triethylamine In methanol at 20℃; for 3h; | |
96% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; |
94% | With sodium methylate In methanol Ambient temperature; | |
94% | With sodium methylate In methanol at 20℃; for 3h; | |
91% | With sodium methylate In methanol for 0.5h; Ambient temperature; | |
89% | With sodium methylate In methanol at 20℃; for 0.5h; | |
With potassium carbonate In methanol | ||
With methanol; sodium methylate at 0℃; for 3h; | 5.c Sodium methoxide (12.5 g) was added to a solution of compound (64 g), obtained from step b above, in methanol (10 mL). The reaction mixture was stirred for 3 hours at 00C. The reaction mixture was then concentrated. The residue thus obtained was purified by column chromatography over silica gel using 30 % ethyl acetate in hexane as eluant to afford the title compound (31 g). Mass (m/z): 261.26 (M+ +1) | |
With water; triethylamine In methanol at 20℃; for 3.5h; | 9.4 Step~4: (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1 ,3-dioxolan-4-yl)-2,2- dimethyltefra hydrofuro[2,3-d][1 ,3]dioxoi-6-ol: To a stirred solution of (3aR,5S,6R,6aR)-5-((R)-2,2-dimethyl-1 ,3-dioxoian-4-yi)~2,2-dimethy tetrahydrofuro [2,3-d][1 ,3]dioxol-6-yl acetate (544.0 g) in MeOH : H20 (1900 mL: 190Q mL) was added Et3N (3,0 eq) and the reaction mixture was stirred at rt for 3.5 h. After completion, the reaction mixture was concentrated in vacuum and codistilied with toluene (3 x 500 mL) to afford the title compound as a black solid (510 g, crude). The crude was used for next step without purification. 1 H NMR (400 MHz; CDCI3): L 5.78 (d, J = 4,0 Hz, 1 H), 4.66 (t, J = 10.2 Hz, 1 H), 4.44 - 4.50 (m, 1 H), 4.2 (m, 1 H), 3.9 ( m, 1 H), 3.03 - 3.09 (m, 1 H), 3.70 (t, J = 4.5 Hz, 1 H), 1 .44 (s, 3H), 1 .42 (s, 3H), 1 .37 (s, 3H). | |
0.60 kg | With sodium methylate In methanol at 20℃; for 1h; | l,2:5,6-di-0-Isopropylidene-a-D-gulofuranose, VI To a solution of 3-O-acetyl- 1,2:5, 6-di-O-isopropylidene-a-D-gulofuranose, V (3.33 mol) in methanol at rt was charged a solution of 25 wt% sodium methoxide in methanol to pH 11. The reaction mixture was stirred at rt for 1 hour, followed by the addition of solid carbon dioxide until the pH was < 7.5. The mixture was concentrated in vacuo at 40 °C using a rotary evaporator and the crude residue was suspended in ethyl acetate (3.9 L) and heated to 60 °C. The mixture was allowed to cool to < 40 °C then filtered, washing with ethyl acetate (1.5 L). The mixture was concentrated in vacuo at 40 °C to a volume of 2.5 L and heated to 60 °C. Heptane (4.65 L) was added and the mixture cooled from 60 °C to 5 °C and stirred for 30 minutes. The product was isolated by filtration washing with heptane (3 x 0.5 L). The filter cake was dried under vacuum at 40 °C to give 0.60 kg (47% over 4 steps from P) of l,2:5,6-di- O-isopropylidene-a-D-gulofuranose as an off-white solid. 'H NMR (400 MHz, CDCli) d 5.78 (d, J= 4.1 Hz, 1H), 4.66 (dd, J= 6.3, 4.1 Hz, 1H), 4.52 - 4.43 (m, 1H), 4.26 - 4.19 (m, 2H), 3.90 (dd, J= 8.6, 5.7 Hz, 1H), 3.72 (dd, J= 8.6, 7.2 Hz, 1H), 2.64 (d, J= 6.4 Hz, 1H), 1.63 (s, 3H), 1.45 (s, 3H), 1.43 (s, 3H),1.38 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride 1.) DMF, room temp., 2 h 2.) DMF, room temp., 2 h; Yield given. Multistep reaction; | ||
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran for 2h; Ambient temperature; | ||
With sodium hydride 1) THF, 1 h, reflux, 2) 1 h, reflux; Yield given. Multistep reaction; |
With tetra-(n-butyl)ammonium iodide; sodium hydride 1) THF, r.t., 45 min, 2) reflux, 1 h; Yield given. Multistep reaction; | ||
With tetra-(n-butyl)ammonium iodide; sodium hydride | ||
With tetra-(n-butyl)ammonium iodide; sodium hydride 1.) THF, 2.) THF, RT, 3 h; Yield given. Multistep reaction; | ||
With sodium hydride 1.) THF, from 0 deg C to RT, 2.) THF, reflux, 1 h; Multistep reaction; | ||
With sodium hydride In N,N-dimethyl-formamide for 1h; Ambient temperature; Yield given; | ||
With sodium hydride | ||
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 0 - 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium hydride In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With pyridine | |
94% | In pyridine at -10 - 0℃; | |
With pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran for 12h; Ambient temperature; | |
With sodium hydride In tetrahydrofuran for 48h; Heating; Yield given; | ||
With sodium hydride In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane Ambient temperature; | ||
With pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With hydrogenchloride In methanol; acetone for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In pyridine at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ruthenium trichloride; sodium tetrahydroborate; potassium metaperiodate; Celite; ammonium chloride; potassium carbonate 1.) chloroform, water 3.) MeOH, 0 deg C, 20 min 4.) r.t., 2 h 5.) 20 min; Yield given. Multistep reaction; | ||
With sodium tetrahydroborate; pyridinium chlorochromate 1.) dichloromethane, room temperature, 3 h 2.) ethanol, water, 0 deg C, 1 h; Yield given. Multistep reaction; | ||
With sodium tetrahydroborate; acetic anhydride 1.) DMSO, 70 deg C, 2.) EtOH, 0 deg C -> room temperature; Yield given. Multistep reaction; |
With sodium tetrahydroborate; acetic anhydride; dimethyl sulfoxide Yield given. Multistep reaction; | ||
Yield given. Multistep reaction; | ||
Multi-step reaction with 2 steps 1: pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 24 h 2: sodium borohydide, ethanol, water / 0.5 h / -20 - 0 °C | ||
Multi-step reaction with 2 steps 1: acetic anhydride / dimethylsulfoxide / 2 h / 70 °C 2: sodium borohydride / ethanol; H2O / 5 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: 65 percent / pyridine / 16 h / 75 °C 2: 90 percent / H2 / Pd / diethyl ether / 24 h 3: 91 percent / CH3ONa / methanol / 0.5 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 2: 1.35 g / sodium borohydride / ethanol; H2O | ||
Multi-step reaction with 2 steps 1: chromium trioxide, pyridine 2: sodium borohydride | ||
Multi-step reaction with 4 steps 1: NaH / tetrahydrofuran / 20 °C 2: 57 percent Chromat. / CF3CO3H, Na2HPO4 / CH2Cl2 / 0 - 20 °C 3: CuSO4 / 24 h / 20 °C 4: 37 percent / KO2, 18C6, / dimethylsulfoxide | ||
Multi-step reaction with 3 steps 1: NaH / tetrahydrofuran / 20 °C 2: KMnO4, NaOH, TEBA-Br / tetrahydrofuran; H2O / 2 h / 20 °C 3: 37 percent / KO2, 18C6, / dimethylsulfoxide | ||
Multi-step reaction with 2 steps 1: 3.20 g / (COCl)2, DMSO / CH2Cl2 / 1 h / -78 °C 2: NaBH4 / ethanol; H2O / 1.5 h / 2 °C | ||
Multi-step reaction with 2 steps 1.1: acetic anhydride; dipyridinium dichromate / 20 °C 1.2: 90 °C 2.1: palladium on activated charcoal; hydrogen / ethyl acetate / 3 h / 2068.65 Torr 2.2: 0.5 h / 20 °C / pH 8 - 10 | ||
Multi-step reaction with 4 steps 1: water; sodium bromide; sodium acetate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / ethyl acetate / 8.5 h / 3 - 7 °C / pH 11.5 - 12.5 / Large scale 2: pyridine / 16 h / 20 - 60 °C / Large scale 3: triethylsilane; palladium 10% on activated carbon; methanol / 20 - 35 °C / Large scale 4: sodium methylate / methanol / 1 h / 20 °C / pH 11 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With sodium hydride In 1,4-dioxane Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium hydroxide; tetrabutylammomium bromide In dichloromethane for 2h; | |
93% | With sodium hydride In N,N-dimethyl-formamide | |
90% | With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran for 24h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With periodic acid In ethyl acetate for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With triethylamine In dichloromethane at -20 - 20℃; for 6.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (1,2:5,6)-di-O-isopropylidene-D-gulose With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium acetate; potassium bromide In water; ethyl acetate for 0.333333h; Stage #2: With triethylamine In water; ethyl acetate for 0.5h; | 5.d Sodium hypochlorite (225 mL, 4% solution) was added dropwise to a solution compound (30 g), obtained from step c above, followed by addition of 2,2,6,6,- tetramethylpiperidine N-oxyl (0.18 g), potassium bromide (10.62 g) and sodium acetate (14.19 g) in ethyl acetate (300 mL) and water (100 mL). After 20 min, triethylamine (3.3 mL) was added dropwise to the above mixture at the same temperature. The reaction mixture was extracted with ethyl acetate after 30 min. The organic layer was dried over anhydrous sodium sulphate. The solvent was evaporated under the reduced pressure to afford the title compound (10.4 g). | |
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In dichloromethane; water at -10℃; | 5 In an open-mouth beaker, a solution of NaBr (0.4 g, 3.89 mmol, 0.1 equiv) in water (2 mL) was added to a solution of diacetone-α-d-gulose (8) (10.0 g, 38.4 mmol, 1.0 equiv) in CH2Cl2 (40 mL) and followed by TEMPO (30 mg, 0.19 mmol, 0.5 mol %). The resulting mixture was cooled to -10 °C (internal temperature), vigorously stirred, and an aqueous solution of NaClO (∼1.6 mol/L, 50 mL, 80 mmol, 2.1 equiv; pH adjusted with NaHCO3 to 9.5) was added drop-wise while keeping the internal temperature at -5 to 0 °C. After addition of the bleach solution, the resulting reaction mixture was stirred for 5 min, the organic layer separated, and washed successively with a solution of KI (0.1 g, 0.6 mmol, 1.6 mol %) in 0.5 M aqueous sulfuric acid (15 mL), a 10% aqueous solution of Na2S2O3 (15 mL), a saturated aqueous solution of NaHCO3 (20 mL), and brine (20 mL). The organic layer was dried (Na2SO4), filtered, evaporated under reduced pressure, and product 9 obtained as a yellowish solid (8.0 g, 80%, purity by NMR ⩾95%).Product 9 was used in the next step without additional purification. The NMR data and other characteristics of product 9 fully corresponded to those reported earlier.16 Rf = 0.37 (Tol/EtOAc = 13:7); mp 69-70 °C; 1H NMR (CDCl3, 300 MHz) δ, ppm: 6.05 (d, 1H, 3J = 4.3 Hz, H-C(1)), 4.45 (d, 1H, 3J = 4.3 Hz, H-C(2)), 4.33 (q, 1H, 3J = 6.6 Hz, H-C(5)), 4.11 (d, 1H, 3J = 6.6 Hz, H-C(4)), 4.09 (dd, 1H, 2J = 8.9 Hz, 3J = 6.6 Hz, Ha-C(6)), 4.02 (dd, 1H, 2J = 8.9 Hz, 3J = 6.6 Hz, Hb-C(6)), 1.54, 1.44, 1.40, 1,36 (4s, 12H, (H3C)2C-O-C(1,2,5,6)). 13C NMR (CDCl3, 100.6 MHz) δ, ppm: 207.1, 115.0, 110.0, 102.6, 81.5, 76.9, 75.5, 65.2, 27.4, 26.9, 26.5, 25.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose With palladium on activated charcoal; hydrogen In ethyl acetate for 3h; Stage #2: With methanol; sodium methylate at 20℃; for 0.5h; | 2 Example 2 Compound I-1 (39.5g, 131.5mmol) was dissolved in ethyl acetate (100mL), Pd/C powder (2.0g) was added, and after stirring, it was placed in a hydrogen (40psi) atmosphere and stirred for 3 hours. TLC (PE: EA=1:1) The reaction is complete, the Pd/C powder is filtered off, and the filtrate is concentrated to obtain a pale yellow syrup intermediate (36.6g, 92%), The light yellow syrup obtained in the previous step was dissolved in methanol (100mL). Sodium methoxide was added to adjust the pH of the reaction solution to 8-10. Stir at room temperature for 30 minutes. TLC (PE:EA=1:1) showed that the reaction was complete. Add 732 H+ resin to adjust the reaction. The liquid is neutral, the resin is filtered off, the filtrate is concentrated, and the light yellow syrup I is separated by column chromatography (PE:EA=3:1), which solidifies (31.2g, 99%) after standing for a long time. |
Multi-step reaction with 2 steps 1: 98 percent / H2 / Pd-C / ethyl acetate / 20 h / 20 °C / 1810.02 Torr 2: 99 percent / H2O; triethylamine / methanol / 3 h / 20 °C | ||
Multi-step reaction with 2 steps 1: 90 percent / H2 / Pd / diethyl ether / 24 h 2: 91 percent / CH3ONa / methanol / 0.5 h / Ambient temperature |
Multi-step reaction with 2 steps 1: 4.2 g / 5percent Pd/C, H2 / Ambient temperature 2: 2.5 g / Amberlite IRA-400 OH form / 40 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / methanol / 120 h / 20 °C 2: sodium methylate / methanol / 3 h / 20 °C / pH 9.5 | ||
Multi-step reaction with 2 steps 1: hydrogen; 5%-palladium/activated carbon / ethanol / 6 h / 20 °C / 1034.32 Torr 2: sodium methylate / methanol / 0.5 h / 20 °C | ||
Multi-step reaction with 2 steps 1: triethylsilane; palladium 10% on activated carbon; methanol / 20 - 35 °C / Large scale 2: sodium methylate / methanol / 1 h / 20 °C / pH 11 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 97 percent / PDC; Ac2O / CH2Cl2 / 2 h / Heating 2: 90 percent / pyridine / 10 h / Heating 3: 98 percent / H2 / Pd-C / ethyl acetate / 20 h / 20 °C / 1810.02 Torr 4: 99 percent / H2O; triethylamine / methanol / 3 h / 20 °C | ||
Multi-step reaction with 4 steps 1: PCC, molecular sieves / CH2Cl2 2: pyridine 3: H2 / Pd black / ethyl acetate 4: K2CO3 / methanol | ||
Multi-step reaction with 2 steps 1: 86 percent / PDC, acetic anhydride / CH2Cl2 / 3 h / 78 °C 2: 1.) Ac2O, 2.) NaBH4 / 1.) pyridine, reflux, 2.) EtOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 15 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine 11: NH2NH2, AcOH 12: 1H-tetrazole 13: m-CPBA 14: H2 / Pd/C 15: K2CO3 / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 14 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine 11: NH2NH2, AcOH 12: 1H-tetrazole 13: m-CPBA 14: H2 / Pd/C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine 11: NH2NH2, AcOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 16 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine 11: NH2NH2, AcOH 12: 1H-tetrazole 13: m-CPBA 14: H2 / Pd/C 15: K2CO3 / methanol 16: a) Amberlite IR-120 resin (Et3NH+ form), b) 1H-tetrazole, pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine 11: NH2NH2, AcOH 12: 1H-tetrazole |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 13 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 5: 60percent aq. AcOH / 60 °C 6: pyridine 7: NaI / acetone 8: NaBH4 / bis-(2-methoxy-ethyl) ether 9: 0.1 N aq. HCl 10: pyridine 11: NH2NH2, AcOH 12: 1H-tetrazole 13: m-CPBA |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether | ||
Multi-step reaction with 4 steps 1: pyridine / CH2Cl2 / Ambient temperature 2: 2-methyl-propan-2-ol; tetrahydrofuran / 12 h / 80 °C 3: 95 percent / N-acetoxy-2-thiopyridone / CH2Cl2 / 0 - 5 °C / Irradiation 4: 87 percent / B(OH)3, H2O / ethanol / 8 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: PCC / CH2Cl2 2: NaBH4 / ethanol | ||
Multi-step reaction with 2 steps 1: PCC, 4A MS / CH2Cl2 / 3 h / Ambient temperature 2: NaBH4 / ethanol; H2O / 1 h / 0 °C | ||
Multi-step reaction with 2 steps 1: pyridinium dichromate, Ac2O / CH2Cl2 / 2 h / 50 °C 2: NaBH4 / ethanol; H2O / 3 h / Ambient temperature |
Multi-step reaction with 2 steps 1: 80 percent / PCC 2: 85 percent / NaBH4 / tetrahydrofuran | ||
Multi-step reaction with 2 steps 1: RuO2, K2CO3, KIO4 / CH2Cl2 / 30 °C 2: 81 percent / NaBH4 / methanol | ||
Multi-step reaction with 2 steps 1: 96 percent / pyridinium dichromate, Ac2O 2: 92 percent / NaBH4 / ethanol; H2O | ||
Multi-step reaction with 2 steps 1: O2 / RuO4 2: NaBH4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NaH, nBu4NI / tetrahydrofuran / 0 - 25 °C 2: 90percent AcOH / H2O / 2.5 h / 40 °C | ||
Multi-step reaction with 2 steps 1: 1.) NaH, 2.) Bu4I / 1.) THF, from 0 deg C to RT, 2.) THF, reflux, 1 h 2: aq. HCl / methanol / 12 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: sodium hydride, tetrabutylammonium iodide 2: acetic acid / H2O |
Multi-step reaction with 2 steps 1: NaH, Bu4NI / tetrahydrofuran / 2 h / Ambient temperature 2: 0.06 N HCl / methanol / 2 h / 55 °C | ||
Multi-step reaction with 2 steps 1: NaH / dimethylformamide / 1.5 h / 25 °C 2: 80percent aq. AcOH / 24 h / 25 °C | ||
Multi-step reaction with 2 steps 1: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, r.t., 45 min, 2) reflux, 1 h 2: conc. HCl / H2O; methanol / 23 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: 1) NaH / 1) DMF, 25 deg C, 30 min, 2) 25 deg C, 1.5 h 2: 2.85 g / aq. AcOH / 24 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 6: NaBH4 / methanol / 0.5 h / Ambient temperature 7: 68 percent / H2 / Pd black / ethanol / 9 h / 45 °C / 760 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature 6: 90 percent / tetrahydrofuran / 12 h / 65 °C 7: 80 percent / Bu3SnH, azobisisobutyronitrile / toluene / 1.5 h / 75 °C 8: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 9: 83 percent / H2 / Pd black / ethanol / 9 h / 45 °C / 760 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 6: NaBH4 / methanol / 0.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature 6: 90 percent / tetrahydrofuran / 12 h / 65 °C 7: 80 percent / Bu3SnH, azobisisobutyronitrile / toluene / 1.5 h / 75 °C 8: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature 6: 90 percent / tetrahydrofuran / 12 h / 65 °C 7: 80 percent / Bu3SnH, azobisisobutyronitrile / toluene / 1.5 h / 75 °C 8: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 9: 83 percent / H2 / Pd black / ethanol / 9 h / 45 °C / 760 Torr 10: 81 percent / pyridine / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature 6: 90 percent / tetrahydrofuran / 12 h / 65 °C 7: 80 percent / Bu3SnH, azobisisobutyronitrile / toluene / 1.5 h / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature 6: 90 percent / tetrahydrofuran / 12 h / 65 °C 7: 80 percent / Bu3SnH, azobisisobutyronitrile / toluene / 1.5 h / 75 °C 8: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 9: 83 percent / H2 / Pd black / ethanol / 9 h / 45 °C / 760 Torr 10: 81 percent / pyridine / 1 h / 0 °C 11: 77 percent / N,N-diisopropylethylamine / CH2Cl2 / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: sodium hydride / dimethylformamide / 1 h / Ambient temperature 2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 5: 97 percent / imidazole / CH2Cl2 / 1 h / Ambient temperature 6: 90 percent / tetrahydrofuran / 12 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C | ||
Multi-step reaction with 3 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C 4: 48 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h 6: 83 percent / H2 / Raney nickel T-4 / ethanol / 3 h | ||
Multi-step reaction with 6 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C 4: 48 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h 6: 83 percent / H2 / Raney nickel T-4 / ethanol / 3 h | ||
Multi-step reaction with 7 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 98 percent / imidazole / dimethylformamide / 7 h / Ambient temperature 3: 99 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 4: 118 mg / propionic acid / 15 h / 135 °C 5: 1.) tetrabutylammonium fluoride / 1.) THF, room temperature, 1 h, 2.) pyridine, 30 min 6: 92 percent / LiAlH4 / tetrahydrofuran / 1 h 7: 83 percent / H2 / Raney nickel T-4 / ethanol / 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C 4: 36 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h 6: 91 percent / H2 / Raney nickel T-4 / ethanol / 3 h | ||
Multi-step reaction with 6 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C 4: 36 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h 6: 91 percent / H2 / Raney nickel T-4 / ethanol / 3 h | ||
Multi-step reaction with 7 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 98 percent / imidazole / dimethylformamide / 7 h / Ambient temperature 3: 99 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 4: 118 mg / propionic acid / 15 h / 135 °C 5: 1.) tetrabutylammonium fluoride / 1.) THF, room temperature, 1 h, 2.) pyridine, 30 min 6: 92 percent / LiAlH4 / tetrahydrofuran / 1 h 7: 91 percent / H2 / Raney nickel T-4 / ethanol / 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C 4: 48 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h | ||
Multi-step reaction with 5 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C 4: 48 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h | ||
Multi-step reaction with 6 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 98 percent / imidazole / dimethylformamide / 7 h / Ambient temperature 3: 99 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 4: 118 mg / propionic acid / 15 h / 135 °C 5: 1.) tetrabutylammonium fluoride / 1.) THF, room temperature, 1 h, 2.) pyridine, 30 min 6: 92 percent / LiAlH4 / tetrahydrofuran / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C 4: 36 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h | ||
Multi-step reaction with 5 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C 4: 36 percent / pyridine / 0.5 h 5: 92 percent / LiAlH4 / tetrahydrofuran / 1 h | ||
Multi-step reaction with 6 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 98 percent / imidazole / dimethylformamide / 7 h / Ambient temperature 3: 99 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 4: 118 mg / propionic acid / 15 h / 135 °C 5: 1.) tetrabutylammonium fluoride / 1.) THF, room temperature, 1 h, 2.) pyridine, 30 min 6: 92 percent / LiAlH4 / tetrahydrofuran / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C 4: 48 percent / pyridine / 0.5 h | ||
Multi-step reaction with 4 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C 4: 48 percent / pyridine / 0.5 h | ||
Multi-step reaction with 5 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 98 percent / imidazole / dimethylformamide / 7 h / Ambient temperature 3: 99 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 4: 118 mg / propionic acid / 15 h / 135 °C 5: 1.) tetrabutylammonium fluoride / 1.) THF, room temperature, 1 h, 2.) pyridine, 30 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 94 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 72 percent / propionic acid / 14 h / 135 °C 4: 36 percent / pyridine / 0.5 h | ||
Multi-step reaction with 4 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 79 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 3: 71 percent / propionic acid / 6.5 h / 135 °C 4: 36 percent / pyridine / 0.5 h | ||
Multi-step reaction with 5 steps 1: 1.) 60percent AcOH, 2.) NaIO4 / 1.) H2O, 14 h, 2.) MeOH, H2O, 1 h, 3.) benzene, room temperature, 1 h 2: 98 percent / imidazole / dimethylformamide / 7 h / Ambient temperature 3: 99 percent / Dibal-H / CH2Cl2; toluene / 1.5 h 4: 118 mg / propionic acid / 15 h / 135 °C 5: 1.) tetrabutylammonium fluoride / 1.) THF, room temperature, 1 h, 2.) pyridine, 30 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: 62 percent / NaH / dioxane / Ambient temperature 2: 92 percent / 80percent aq. acetic acid / Ambient temperature 3: sodium periodate / H2O / 0.33 h 4: sodium borohydride / H2O / 0.33 h 5: 79 percent / pyridine / 12 h / Ambient temperature 6: 93.9 percent / NaI / butan-2-one / 2 h / Heating 7: 54.2 percent / phloroglucinol monohydrate, sodium nitrite / dimethylsulfoxide / 96 h / Ambient temperature 8: KF, tetrabutylammonium iodide / toluene / 2.5 h / Ambient temperature 9: H2 / Raney nickel T-4 / ethyl acetate; acetic acid / 20 h / 4045.3 Torr 10: 4.7 percent / methanol / 0.17 h / Ambient temperature | ||
Multi-step reaction with 12 steps 1: 62 percent / NaH / dioxane / Ambient temperature 2: 92 percent / 80percent aq. acetic acid / Ambient temperature 3: sodium periodate / H2O / 0.33 h 4: sodium borohydride / H2O / 0.33 h 5: 79 percent / pyridine / 12 h / Ambient temperature 6: 93.9 percent / NaI / butan-2-one / 2 h / Heating 7: 54.2 percent / phloroglucinol monohydrate, sodium nitrite / dimethylsulfoxide / 96 h / Ambient temperature 8: KF, tetrabutylammonium iodide / toluene / 2.5 h / Ambient temperature 9: H2 / Raney nickel T-4 / ethyl acetate; acetic acid / 20 h / 4045.3 Torr 10: methanol / 0.17 h / Ambient temperature 11: 1.) phosphoric acid, DCC; 2.) oxalic acid / 1.) toluene, pyridine, DMSO, room temp., 3 h.; 2.) toluene, pyridine, DMSO, methanol, 30 min. 12: 29 percent / sodium borohydride / H2O; ethanol / 0.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: pyridine / CH2Cl2 / Ambient temperature 2: 2-methyl-propan-2-ol; tetrahydrofuran / 12 h / 80 °C 3: 95 percent / N-acetoxy-2-thiopyridone / CH2Cl2 / 0 - 5 °C / Irradiation 4: 87 percent / B(OH)3, H2O / ethanol / 8 h / 80 °C 5: 90 percent / pyridine / CH2Cl2 / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / Ambient temperature 2: 2-methyl-propan-2-ol; tetrahydrofuran / 12 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine / CH2Cl2 / Ambient temperature 2: 2-methyl-propan-2-ol; tetrahydrofuran / 12 h / 80 °C 3: 95 percent / N-acetoxy-2-thiopyridone / CH2Cl2 / 0 - 5 °C / Irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 94 percent / pyridine / -10 - 0 °C 2: 59 percent / H2O, Dowex 50X 4-400 (H+) / methanol; dioxane / 72 h / 0 °C 3: 70 percent / LiN3, PPh3, CBr4 / dimethylformamide / 18 h / 0 deg C to room temperature 4: 1.) H2, 2.) NaOAc / 1.) 10percent Pd/C / 1.) EtOH, room temperature, 36 h, 2.) EtOH, reflux, 24 h 5: Et3N / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, overnight | ||
Multi-step reaction with 7 steps 1: 95 percent / pyridine 2: 74 percent / 0.8percent aq. H2SO4 / dioxane; methanol / 23 h / Ambient temperature 3: 94 percent / CBr4, PPh3 / tetrahydrofuran / 11 h / Ambient temperature 4: 96 percent / NaN3 / dimethylformamide / 8 h / 45 °C 5: H2 / Raney nickel / methanol / 24 h / Ambient temperature 6: NaOAc / ethanol / 15 h / Heating 7: Na2CO3 / acetone; H2O / 2 h / 0 °C | ||
Multi-step reaction with 7 steps 1: 95 percent / pyridine 2: 74 percent / aq. H2SO4 3: Ph3P, CBr4 / tetrahydrofuran 4: NaN3 / dimethylformamide 5: hydrogen / Raney Ni 6: NaOAc / ethanol / Heating 7: Na2CO3 / acetone; H2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 94 percent / pyridine / -10 - 0 °C 2: 59 percent / H2O, Dowex 50X 4-400 (H+) / methanol; dioxane / 72 h / 0 °C 3: 70 percent / LiN3, PPh3, CBr4 / dimethylformamide / 18 h / 0 deg C to room temperature 4: 1.) H2, 2.) NaOAc / 1.) 10percent Pd/C / 1.) EtOH, room temperature, 36 h, 2.) EtOH, reflux, 24 h | ||
Multi-step reaction with 6 steps 1: 95 percent / pyridine 2: 74 percent / 0.8percent aq. H2SO4 / dioxane; methanol / 23 h / Ambient temperature 3: 94 percent / CBr4, PPh3 / tetrahydrofuran / 11 h / Ambient temperature 4: 96 percent / NaN3 / dimethylformamide / 8 h / 45 °C 5: H2 / Raney nickel / methanol / 24 h / Ambient temperature 6: NaOAc / ethanol / 15 h / Heating | ||
Multi-step reaction with 6 steps 1: 95 percent / pyridine 2: 74 percent / aq. H2SO4 3: Ph3P, CBr4 / tetrahydrofuran 4: NaN3 / dimethylformamide 5: hydrogen / Raney Ni 6: NaOAc / ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 13 steps 1: NaH / dimethylformamide / 1.5 h / 25 °C 2: 80percent aq. AcOH / 24 h / 25 °C 3: pyridine / CH2Cl2 / 1 h / 2 °C 4: (COCl)2, DMSO, Et3N / CH2Cl2 / 1 h / -78 °C 5: 90 percent / KF / 18-crown-6 / dimethylformamide / 3 h / 25 °C 6: p-TsOH*H2O / 3 h / 25 °C 7: NaBH4 / aq. ethanol / 2 h / 25 °C 8: 82 percent / 80percent aq. AcOH / 15 h / 80 °C 9: Pb(OAc)4 / benzene / 0.67 h / 25 °C 10: KF / 18-crown-6 / dimethylformamide / 3.5 h / 2 °C 11: Ac2O / p-TsOH*H2O / 1.5 h / 25 °C 12: 1.) 28percent aq. NH4OH / 2.) p-TsOH*H2O / 1.) 95percent aq. EtOH, 25 deg C, 2 h, 2.) 25 deg C, 2 h 13: 63 percent / n-Bu3SnH, AIBN / benzene / 3 h / 80 °C | ||
Multi-step reaction with 13 steps 1: NaH / dimethylformamide / 1.5 h / 25 °C 2: 80percent aq. AcOH / 24 h / 25 °C 3: pyridine / CH2Cl2 / 1 h / 2 °C 4: (COCl)2, DMSO, Et3N / CH2Cl2 / 1 h / -78 °C 5: 90 percent / KF / 18-crown-6 / dimethylformamide / 3 h / 25 °C 6: p-TsOH*H2O / 3 h / 25 °C 7: NaBH4 / aq. ethanol / 2 h / 25 °C 8: 82 percent / 80percent aq. AcOH / 15 h / 80 °C 9: Pb(OAc)4 / benzene / 0.67 h / 25 °C 10: KF / 18-crown-6 / dimethylformamide / 3.5 h / 2 °C 11: Ac2O / p-TsOH*H2O / 1.5 h / 25 °C 12: 1.) 28percent aq. NH4OH / 2.) p-TsOH*H2O / 1.) 95percent aq. EtOH, 25 deg C, 2 h, 2.) 25 deg C, 2 h 13: 62 percent / n-Bu3SnH, AIBN / benzene / 3 h / 80 °C | ||
Multi-step reaction with 14 steps 1: 1) NaH / 1) DMF, 25 deg C, 30 min, 2) 25 deg C, 1.5 h 2: 2.85 g / aq. AcOH / 24 h / 25 °C 3: pyridine / CH2Cl2 / 1 h / 2 °C 4: 770 mg / (COCl)2, DMSO / CH2Cl2 / 1 h / -78 °C 5: 90 percent / KF, 18-crown-6 / dimethylformamide / 3 h / 25 °C 6: p-TsOH*H2O / 3 h / 25 °C 7: NaBH4 / ethanol; H2O / 2 h / 25 °C 8: 82 percent / aq. AcOH / 15 h / 80 °C 9: Pb(OAc)4 / benzene / 0.67 h / 25 °C 10: KF, 18-crown-6 / dimethylformamide / 3.5 h / 2 °C 11: 31 percent / Ac2O, p-TsOH*H2O / 1.5 h / 25 °C 12: aq. NH4OH / ethanol / 2 h / 25 °C 13: p-TsOH*H2O / 2 h / 25 °C 14: 63 percent / n-Bu3SnH, AIBN / benzene / 3 h / 80 °C |
Multi-step reaction with 14 steps 1: 1) NaH / 1) DMF, 25 deg C, 30 min, 2) 25 deg C, 1.5 h 2: 2.85 g / aq. AcOH / 24 h / 25 °C 3: pyridine / CH2Cl2 / 1 h / 2 °C 4: 770 mg / (COCl)2, DMSO / CH2Cl2 / 1 h / -78 °C 5: 90 percent / KF, 18-crown-6 / dimethylformamide / 3 h / 25 °C 6: p-TsOH*H2O / 3 h / 25 °C 7: NaBH4 / ethanol; H2O / 2 h / 25 °C 8: 82 percent / aq. AcOH / 15 h / 80 °C 9: Pb(OAc)4 / benzene / 0.67 h / 25 °C 10: KF, 18-crown-6 / dimethylformamide / 3.5 h / 2 °C 11: 31 percent / Ac2O, p-TsOH*H2O / 1.5 h / 25 °C 12: aq. NH4OH / ethanol / 2 h / 25 °C 13: p-TsOH*H2O / 2 h / 25 °C 14: 62 percent / n-Bu3SnH, AIBN / benzene / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 92 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / 1 h / -78 °C 2: NaBH4 / aq. ethanol / 1.5 h / 2 °C | ||
Multi-step reaction with 2 steps 1: pyridinium chlorochromate, molecular sieve / CH2Cl2 2: NaBH4 / ethanol | ||
Multi-step reaction with 2 steps 1: PCC, mol. sieves / CH2Cl2 2: NaBH4 / ethanol |
Multi-step reaction with 2 steps 1: Ru2O, NaIO4 2: NaBH4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h | ||
Multi-step reaction with 11 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 80 percent / tetrahydrofuran / 6 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 13 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h 12: KH / tetrahydrofuran / 25 °C 13: Amberlite IR-120 / H2O / 8 h / 90 °C | ||
Multi-step reaction with 13 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 80 percent / tetrahydrofuran / 6 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h 12: KH / tetrahydrofuran / 25 °C 13: Amberlite IR-120 / H2O / 8 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h 12: KH / tetrahydrofuran / 25 °C | ||
Multi-step reaction with 12 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 80 percent / tetrahydrofuran / 6 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h 12: KH / tetrahydrofuran / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 60 percent / tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: H2 / Pd-C / ethanol / 0.5 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C | ||
Multi-step reaction with 10 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 80 percent / tetrahydrofuran / 6 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 60 percent / tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: H2 / Pd-C / ethanol / 0.5 h / 25 °C 10: KH / tetrahydrofuran / 6 h / 60 °C 11: 98 percent / Amberlite IR-120 / H2O / 8 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 60 percent / tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: H2 / Pd-C / ethanol / 0.5 h / 25 °C 10: KH / tetrahydrofuran / 6 h / 60 °C 11: 98 percent / Amberlite IR-120 / H2O / 8 h / 90 °C 12: 1.) NaBH4, 2.) NaIO4 / 1.) EtOH, 25 deg C, 48 h, 2.) EtOH-H2O, 0 deg C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 60 percent / tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: H2 / Pd-C / ethanol / 0.5 h / 25 °C 10: KH / tetrahydrofuran / 6 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C | ||
Multi-step reaction with 9 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 80 percent / tetrahydrofuran / 6 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 13 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 60 percent / tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: H2 / Pd-C / ethanol / 0.5 h / 25 °C 10: KH / tetrahydrofuran / 6 h / 60 °C 11: 98 percent / Amberlite IR-120 / H2O / 8 h / 90 °C 12: 1.) NaBH4, 2.) NaIO4 / 1.) EtOH, 25 deg C, 48 h, 2.) EtOH-H2O, 0 deg C 13: 87 percent / toluene / 3 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 14 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: tetrahydrofuran / 48 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h 12: KH / tetrahydrofuran / 25 °C 13: Amberlite IR-120 / H2O / 8 h / 90 °C 14: toluene / 48 h / 25 °C | ||
Multi-step reaction with 14 steps 1: pyridine 2: aq. H2SO4 3: 1.) (EtO)3CH / 2.) heating 4: K2CO3, MeOH 5: pyridine 6: 80 percent / tetrahydrofuran / 6 h / 25 °C 7: 1.) Dibal, 2.) H2SO4 / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) 25 deg C , 0.5 h 8: LiAlH4 / diethyl ether / 0.5 h / 0 °C 9: Et3N / CH2Cl2 / -20 °C 10: LiAlH4 / tetrahydrofuran / 0.5 h / 60 °C 11: 1.) diisoamylborane, 2.) NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 1 h 12: KH / tetrahydrofuran / 25 °C 13: Amberlite IR-120 / H2O / 8 h / 90 °C 14: toluene / 48 h / 25 °C |