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
There total 10 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 which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 7 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
With
potassium hydroxide; sodium tetrahydroborate; hydrogen; dihydrogen peroxide; sodium methylate; sodium hydride; magnesium sulfate; 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 8 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
With
potassium hydroxide; sodium tetrahydroborate; hydrogen; dihydrogen peroxide; sodium methylate; titanium tetrachloride; sodium hydride; magnesium sulfate; 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 7 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
With
potassium hydroxide; sodium tetrahydroborate; hydrogen; dihydrogen peroxide; sodium methylate; sodium hydride; magnesium sulfate; 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
