(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

Base Information

Chemical Name:(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
CAS No.:320748-69-4
Molecular Formula:C₁₈H₂₃NO₅
Molecular Weight:333.384
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 8 articles about (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 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: 86.0%

: C₂₀H₂₅NO₆

: 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

Guidance literature:: With sodium methylate; In methanol; at 25 ℃; for 3h; Inert atmosphere;
DOI:10.1002/anie.201602755

Reference yield: 68.0%

: 320748-67-2
(2S,3aS,7aS)-6-oxo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 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

: 320748-68-3
1-benzyl 2-methyl (2S,3aS,6S,7aS)-6-hydroxyoctahydro-1H-indole-1,2-dicarboxylate

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 ℃; for 3h;
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

: 320748-69-4
(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

Guidance literature:: Multi-step reaction with 5 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

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