Technology Process of 3-[(1S,2R)-1-Hydroxy-2-methoxycarbonyl-2-(4-nitro-benzenesulfonyloxy)-ethyl]-2-phenylsulfanyl-indole-1-carboxylic acid benzyl ester
There total 6 articles about 3-[(1S,2R)-1-Hydroxy-2-methoxycarbonyl-2-(4-nitro-benzenesulfonyloxy)-ethyl]-2-phenylsulfanyl-indole-1-carboxylic acid benzyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: NaH / N,N-dimethyl-acetamide
1.2: 83 percent / N,N-dimethyl-acetamide / 2.5 h / 90 °C
2.1: n-BuLi / hexane; 1,2-dimethoxy-ethane
2.2: 81 percent / hexane; 1,2-dimethoxy-ethane / 40 h / Heating
3.1: NaH / tetrahydrofuran / 2 h
3.2: tetrahydrofuran / 15 h
4.1: potassium ferricyanide; K2CO3; MeSO2NH2 / K2OsO2(OH)4; (DHQ)2PHAL / H2O; 2-methyl-propan-2-ol / 15 h
4.2: 85 percent / sodium sulfite / H2O; 2-methyl-propan-2-ol / 0.5 h
5.1: Et3N / CH2Cl2 / 15 h / 0 °C
With
n-butyllithium; methanesulfonamide; sodium hydride; potassium carbonate; triethylamine; potassium hexacyanoferrate(III);
Hydroquinone 1,4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI);
In
tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; N,N-dimethyl acetamide; water; tert-butyl alcohol;
4.1: Sharpless asymmetric bishydroxylation;
DOI:10.1021/ol048974+
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: NaH / N,N-dimethyl-acetamide
1.2: 83 percent / N,N-dimethyl-acetamide / 2.5 h / 90 °C
2.1: n-BuLi / hexane; 1,2-dimethoxy-ethane
2.2: 81 percent / hexane; 1,2-dimethoxy-ethane / 40 h / Heating
3.1: NaH / tetrahydrofuran / 2 h
3.2: tetrahydrofuran / 15 h
4.1: potassium ferricyanide; K2CO3; MeSO2NH2 / K2OsO2(OH)4; (DHQ)2PHAL / H2O; 2-methyl-propan-2-ol / 15 h
4.2: 85 percent / sodium sulfite / H2O; 2-methyl-propan-2-ol / 0.5 h
5.1: Et3N / CH2Cl2 / 15 h / 0 °C
With
n-butyllithium; methanesulfonamide; sodium hydride; potassium carbonate; triethylamine; potassium hexacyanoferrate(III);
Hydroquinone 1,4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI);
In
tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; N,N-dimethyl acetamide; water; tert-butyl alcohol;
4.1: Sharpless asymmetric bishydroxylation;
DOI:10.1021/ol048974+
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: n-BuLi / hexane; 1,2-dimethoxy-ethane
1.2: 81 percent / hexane; 1,2-dimethoxy-ethane / 40 h / Heating
2.1: NaH / tetrahydrofuran / 2 h
2.2: tetrahydrofuran / 15 h
3.1: potassium ferricyanide; K2CO3; MeSO2NH2 / K2OsO2(OH)4; (DHQ)2PHAL / H2O; 2-methyl-propan-2-ol / 15 h
3.2: 85 percent / sodium sulfite / H2O; 2-methyl-propan-2-ol / 0.5 h
4.1: Et3N / CH2Cl2 / 15 h / 0 °C
With
n-butyllithium; methanesulfonamide; sodium hydride; potassium carbonate; triethylamine; potassium hexacyanoferrate(III);
Hydroquinone 1,4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI);
In
tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; water; tert-butyl alcohol;
3.1: Sharpless asymmetric bishydroxylation;
DOI:10.1021/ol048974+
