Technology Process of (3aR,4R,6S,7aR)-6-Benzyloxymethyl-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid ethyl ester
There total 11 articles about (3aR,4R,6S,7aR)-6-Benzyloxymethyl-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid ethyl ester which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1: H2 / Pd/C 10percent / ethyl acetate / 12 h / 2068.6 Torr
2: 100 percent / CH3ONa / methanol / 1 h
3: 87 percent / p-toluenosulfonic acid, MgSO4 / acetone / 3 h / Ambient temperature
4: 1.) LDA / 1.) THF, -75 deg C, 30 min, 2.) THF, from -75 deg C to RT
5: 91 percent / NaBH4 / methanol / 2 h / -10 °C
6: 79 percent / NaH / dimethylformamide; diethyl ether / Ambient temperature
7: 0.5 M aq KOH, 35percent H2O2 / 24 h / Heating
8: Cs2CO3 / dimethylformamide / Ambient temperature
With
potassium hydroxide; sodium tetrahydroborate; hydrogen; dihydrogen peroxide; sodium methylate; sodium hydride; magnesium sulfate; caesium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide;
palladium on activated charcoal;
In
methanol; diethyl ether; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00226a010
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 82 percent / TiCl4 / CH2Cl2 / 4 h / Ambient temperature
2: 68 percent / H2 / Pd/C 10percent / pyridine; toluene / 8 h / 2068.6 Torr
3: 100 percent / CH3ONa / methanol / 1 h
4: 87 percent / p-toluenosulfonic acid, MgSO4 / acetone / 3 h / Ambient temperature
5: 1.) LDA / 1.) THF, -75 deg C, 30 min, 2.) THF, from -75 deg C to RT
6: 91 percent / NaBH4 / methanol / 2 h / -10 °C
7: 79 percent / NaH / dimethylformamide; diethyl ether / Ambient temperature
8: 0.5 M aq KOH, 35percent H2O2 / 24 h / Heating
9: Cs2CO3 / dimethylformamide / Ambient temperature
With
potassium hydroxide; sodium tetrahydroborate; hydrogen; dihydrogen peroxide; sodium methylate; titanium tetrachloride; sodium hydride; magnesium sulfate; caesium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide;
palladium on activated charcoal;
In
pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/jo00226a010
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 68 percent / H2 / Pd/C 10percent / pyridine; toluene / 8 h / 2068.6 Torr
2: 100 percent / CH3ONa / methanol / 1 h
3: 87 percent / p-toluenosulfonic acid, MgSO4 / acetone / 3 h / Ambient temperature
4: 1.) LDA / 1.) THF, -75 deg C, 30 min, 2.) THF, from -75 deg C to RT
5: 91 percent / NaBH4 / methanol / 2 h / -10 °C
6: 79 percent / NaH / dimethylformamide; diethyl ether / Ambient temperature
7: 0.5 M aq KOH, 35percent H2O2 / 24 h / Heating
8: Cs2CO3 / dimethylformamide / Ambient temperature
With
potassium hydroxide; sodium tetrahydroborate; hydrogen; dihydrogen peroxide; sodium methylate; sodium hydride; magnesium sulfate; caesium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide;
palladium on activated charcoal;
In
pyridine; methanol; diethyl ether; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/jo00226a010
