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

Base Information

• Chemical Name: dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate
• CAS No.: 136057-11-9
• Molecular Formula: C₂₀H₂₀N₂O₆S
• Molecular Weight: 416.455
• Mol file: 136057-11-9.mol

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

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

Chemical Property:

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

DIMETHYL-2(S),3A(R),8A(S)-(+)-HEXAHYDRO-8-(PHENYLSULFONYL)PYRROLO[2,3-B]INDOLE-1,2-DICARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 6 articles about dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-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: 80.0%

L-(2β,3aα,8aα)-1,2,3,3a,8,8a-hexahydro-1,2-dimethoxycarbonylpyrrolo<2,3-b>indole (79465-82-0) + benzenesulfonyl chloride (98-09-9) → dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate (136057-11-9)

Guidance literature:

With pyridine; at 0 - 20 ℃;

DOI:10.1002/ejoc.201101057

Reference yield: 60.0%

(+)-(2S,3aS,8aS)-3a-Bromo-1,2-bis(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole (151414-50-5) → C40H38N4O12S2 + dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate (136057-11-9)

Guidance literature:

chlorotris(triphenylphosphine)cobalt(I); In acetone; at 23 ℃; for 0.25h;

DOI:10.1002/anie.200700705

Reference yield:

Nα-methoxycarbonyl-D-tryptophan methyl ester (79631-04-2) → dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate (136057-11-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85percent H₃PO₄

2: pyridine

With phosphoric acid; In pyridine;

DOI:10.1016/0040-4020(95)00001-O

upstream raw materials:

L-(2β,3aα,8aα)-1,2,3,3a,8,8a-hexahydro-1,2-dimethoxycarbonylpyrrolo<2,3-b>indole

benzenesulfonyl chloride

(+)-(2S,3aS,8aS)-3a-Bromo-1,2-bis(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole

N_α-methoxycarbonyl-D-tryptophan methyl ester

Downstream raw materials:

(+)-(2S,3aR,8aS)-2-(Hydroxymethyl)-1-(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole

(+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid

(2S,3aR,8aS)-8-Benzenesulfonyl-2-(imidazole-1-carbothioyloxymethyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester

(S)-3-(1-Benzenesulfonyl-1H-indol-3-yl)-2-methoxycarbonylamino-2-methyl-propionic acid methyl ester