6-(tert-butyldimethylsilanyloxy)-(2S,3,3aR,6S,7,7aR)-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

Chemical Name:6-(tert-butyldimethylsilanyloxy)-(2S,3,3aR,6S,7,7aR)-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
CAS No.:486421-47-0
Molecular Formula:C₂₄H₃₅NO₅Si
Molecular Weight:445.631
Hs Code.:

Synonyms:6-(tert-butyldimethylsilanyloxy)-(2S,3,3aR,6S,7,7aR)-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Chemical Property of 6-(tert-butyldimethylsilanyloxy)-(2S,3,3aR,6S,7,7aR)-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Technology Process of 6-(tert-butyldimethylsilanyloxy)-(2S,3,3aR,6S,7,7aR)-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 5 articles about 6-(tert-butyldimethylsilanyloxy)-(2S,3,3aR,6S,7,7aR)-hexahydroindole-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: 97.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 171523-46-9
(2S,3aR,6S,7aR)-6-hydroxy-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 486421-47-0
6-(tert-butyldimethylsilanyloxy)-(2S,3,3aR,6S,7,7aR)-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/ja044280k

Reference yield:

: 144534-49-6
(2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 486421-47-0
6-(tert-butyldimethylsilanyloxy)-(2S,3,3aR,6S,7,7aR)-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 26 g / dimethylaminopyridine; pyridine / CH₂Cl₂ / 20 h / Heating

2: 97 percent / cerium(III) chloride heptahydrate; NaBH₄ / tetrahydrofuran; methanol / 15 h / 0 °C

3: 93 percent / Pd₂(dba)3*CHCl₃; tribenzylphosphine; triethylamine / formic acid / tetrahydrofuran / 16 h / Heating

4: 97 percent / imidazole; dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; 1H-imidazole; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; cerium(III) chloride; triethylamine; tribenzylphosphine; formic acid; In tetrahydrofuran; methanol; dichloromethane; 2: Luche reduction;
DOI:10.1021/ja044280k

Reference yield:

: 171523-63-0
<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

: 486421-47-0
6-(tert-butyldimethylsilanyloxy)-(2S,3,3aR,6S,7,7aR)-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / cerium(III) chloride heptahydrate; NaBH₄ / tetrahydrofuran; methanol / 15 h / 0 °C

2: 93 percent / Pd₂(dba)3*CHCl₃; tribenzylphosphine; triethylamine / formic acid / tetrahydrofuran / 16 h / Heating

3: 97 percent / imidazole; dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; cerium(III) chloride; triethylamine; tribenzylphosphine; formic acid; In tetrahydrofuran; methanol; dichloromethane; 1: Luche reduction;
DOI:10.1021/ja044280k