dimethyl (2S,3aS,8aR)-8-5-methoxy-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Base Information

Chemical Name:dimethyl (2S,3aS,8aR)-8-5-methoxy-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
CAS No.:145919-17-1
Molecular Formula:C₂₇H₃₆N₂O₈SSi
Molecular Weight:576.743
Hs Code.:

dimethyl (2S,3aS,8aR)-8-5-methoxy-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Synonyms:dimethyl (2S,3aS,8aR)-8-5-methoxy-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

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Chemical Property of dimethyl (2S,3aS,8aR)-8-5-methoxy-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

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Technology Process of dimethyl (2S,3aS,8aR)-8-5-methoxy-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

There total 1 articles about dimethyl (2S,3aS,8aR)-8-5-methoxy-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate 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:

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: dimethyl (2R,3aS,8aR)-5-methoxy-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

: 145919-17-1
dimethyl (2S,3aS,8aR)-8-5-methoxy-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Guidance literature:: With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, 1 h, 2.) THF, -78 deg C, 4 h;
DOI:10.1021/jm00055a001

Reference yield: 62.0%

: 145919-17-1
dimethyl (2S,3aS,8aR)-8-5-methoxy-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

: 145919-19-3
dimethyl (2S,3aS,8aR)-2-(hydroxymethyl)-5-methoxy-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 1h;
DOI:10.1021/jm00055a001

Reference yield:

: 145919-17-1
dimethyl (2S,3aS,8aR)-8-5-methoxy-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

: α(R)-(fluoromethyl)-5-hydroxy-N_b-(methoxycarbonyl)-N_a-(phenylsulfonyl)tryptophan methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 62 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / 0 - 20 °C

2: 32 percent / DAST / CH₂Cl₂ / 3 h / Ambient temperature

3: 94 percent / trifluoroacetic acid / 2 h / Ambient temperature

4: 65 percent / boron tribromide / CH₂Cl₂ / 2.5 h / -78 - 20 °C

With boron trifluoride diethyl etherate; boron tribromide; 4,4'-diaminostilbene-2,2'-disulfonic acid; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/jm00055a001