dimethyl (2R,3aR,8aS)-8-(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 (2R,3aR,8aS)-8-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
• CAS No.: 145814-41-1
• Molecular Formula: C₂₆H₃₄N₂O₇SSi
• Molecular Weight: 546.717

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

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

Chemical Property:

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Technology Process of dimethyl (2R,3aR,8aS)-8-(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 (2R,3aR,8aS)-8-(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:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) + dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate (136057-11-9) → dimethyl (2R,3aR,8aS)-8-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145814-41-1)

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: 90.0%

dimethyl (2R,3aR,8aS)-8-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145814-41-1) → α(R)-(hydroxymethyl)-Nb-(methoxycarbonyl)-N-a-(phenylsulfonyl)tryptophan methyl ester

Guidance literature:

With trifluoroacetic acid; for 1h; Ambient temperature;

DOI:10.1021/jm00055a001

Reference yield: 85.0%

dimethyl (2R,3aR,8aS)-8-(phenylsulfonyl)-2-<<2-(trimethylsilyl)ethoxy>methyl>-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145814-41-1) → dimethyl (2R,3aR,8aS)-2-(hydroxymethyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (145814-46-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1021/jm00055a001

upstream raw materials:

(2-trimethylethylsilylethoxy)methyl chloride

dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate

Downstream raw materials:

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

α(S)-(fluoromethyl)tryptophan

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