(2S,3aR,7aR)-3a-Benzoyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,7a-tetrahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

• Chemical Name: (2S,3aR,7aR)-3a-Benzoyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,7a-tetrahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS No.: 185394-43-8
• Molecular Formula: C₃₁H₃₇NO₇Si
• Molecular Weight: 563.723

Synonyms:(2S,3aR,7aR)-3a-Benzoyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,7a-tetrahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property of (2S,3aR,7aR)-3a-Benzoyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,7a-tetrahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property:

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Technology Process of (2S,3aR,7aR)-3a-Benzoyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,7a-tetrahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 2 articles about (2S,3aR,7aR)-3a-Benzoyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,7a-tetrahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl 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:

Reference yield: 84.0%

t-butyldimethylsiyl triflate (69739-34-0) + <2S-(2β,3aβ,7aβ)>-2,3,3a,6,7,7a-hexahydro-3a-benzoyloxy-6-oxo-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester (171523-63-0) → (2S,3aR,7aR)-3a-Benzoyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,7a-tetrahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (185394-43-8)

Guidance literature:

With triethylamine; In dichloromethane; for 0.5h;

DOI:10.1016/0040-4020(96)00871-X

Reference yield:

(2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (144534-49-6) → (2S,3aR,7aR)-3a-Benzoyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,7a-tetrahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (185394-43-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / DMAP, Et₃N / CH₂Cl₂ / 48 h / Heating

2: 84 percent / Et₃N / CH₂Cl₂ / 0.5 h

With dmap; triethylamine; In dichloromethane;

DOI:10.1016/0040-4020(96)00871-X

Reference yield:

(2S,3aR,7aR)-3a-Benzoyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,7a-tetrahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (185394-43-8) → (1aS,3aR,5S,6aR,6bS)-3a-Benzoyloxy-1a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,4,5,6a,6b-hexahydro-1-oxa-6-aza-cyclopropa[e]indene-5,6-dicarboxylic acid 6-benzyl ester 5-methyl ester (185394-44-9)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; at 0 ℃; for 0.5h;

DOI:10.1016/0040-4020(96)00871-X

upstream raw materials:

t-butyldimethylsiyl triflate

<2S-(2β,3aβ,7aβ)>-2,3,3a,6,7,7a-hexahydro-3a-benzoyloxy-6-oxo-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester

(2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Downstream raw materials:

(1aS,3aR,5S,6aR,6bS)-3a-Benzoyloxy-1a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,4,5,6a,6b-hexahydro-1-oxa-6-aza-cyclopropa[e]indene-5,6-dicarboxylic acid 6-benzyl ester 5-methyl ester

(2S,3aR,7S,7aR)-3a-Benzoyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-oxo-2,3,3a,6,7,7a-hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(2S,3aR,6R,7S,7aR)-3a-Benzoyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-2,3,3a,6,7,7a-hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(2S,3aR,6R,7S,7aR)-6-Acetoxy-3a-benzoyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,6,7,7a-hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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