(2S,3aS,6R,7aS)-6-(tert-butyldimethylsiloxy)-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

Chemical Name:(2S,3aS,6R,7aS)-6-(tert-butyldimethylsiloxy)-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
CAS No.:320748-70-7
Molecular Formula:C₂₄H₃₇NO₅Si
Molecular Weight:447.647
Hs Code.:

Synonyms:(2S,3aS,6R,7aS)-6-(tert-butyldimethylsiloxy)-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Chemical Property of (2S,3aS,6R,7aS)-6-(tert-butyldimethylsiloxy)-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Technology Process of (2S,3aS,6R,7aS)-6-(tert-butyldimethylsiloxy)-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 8 articles about (2S,3aS,6R,7aS)-6-(tert-butyldimethylsiloxy)-2,3,3a,4,5,6,7,7a-octahydroindole-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: 87.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 320748-69-4
(2S,3aS,6R,7aS)-6-hydroxy-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 320748-70-7
(2S,3aS,6R,7aS)-6-(tert-butyldimethylsiloxy)-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1021/ol006759x

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

: 320748-70-7
(2S,3aS,6R,7aS)-6-(tert-butyldimethylsiloxy)-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 90 percent / DMAP; pyridine / CH₂Cl₂ / 50 h / 40 °C

2.1: 78 percent / NaHCO₃ / dimethylsulfoxide / 1 h / 90 °C

3.1: AcOH / tetrahydrofuran

3.2: 75 percent / zinc; BrCH₂CH₂Br; TMSCl / tetrahydrofuran / 9 h / 65 °C

4.1: 95 percent / H₂ / PtO₂ / acetic acid; ethanol / 1 h / 0 °C / 760.05 Torr

5.1: 68 percent / L-selectride / tetrahydrofuran / 3 h / -78 °C

6.1: 87 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

With pyridine; 1H-imidazole; dmap; hydrogen; L-Selectride; sodium hydrogencarbonate; acetic acid; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; acetic acid; dimethyl sulfoxide;
DOI:10.1021/ol006759x

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

: 320748-70-7
(2S,3aS,6R,7aS)-6-(tert-butyldimethylsiloxy)-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 78 percent / NaHCO₃ / dimethylsulfoxide / 1 h / 90 °C

2.1: AcOH / tetrahydrofuran

2.2: 75 percent / zinc; BrCH₂CH₂Br; TMSCl / tetrahydrofuran / 9 h / 65 °C

3.1: 95 percent / H₂ / PtO₂ / acetic acid; ethanol / 1 h / 0 °C / 760.05 Torr

4.1: 68 percent / L-selectride / tetrahydrofuran / 3 h / -78 °C

5.1: 87 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

With 1H-imidazole; hydrogen; L-Selectride; sodium hydrogencarbonate; acetic acid; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; acetic acid; dimethyl sulfoxide;
DOI:10.1021/ol006759x