dimethyl (2S,3aR,8aS)-2-benzyl-8-(p-tolylsulphonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Base Information

• Chemical Name: dimethyl (2S,3aR,8aS)-2-benzyl-8-(p-tolylsulphonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
• CAS No.: 127628-12-0
• Molecular Formula: C₂₈H₂₈N₂O₆S
• Molecular Weight: 520.606

Synonyms:dimethyl (2S,3aR,8aS)-2-benzyl-8-(p-tolylsulphonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Chemical Property of dimethyl (2S,3aR,8aS)-2-benzyl-8-(p-tolylsulphonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of dimethyl (2S,3aR,8aS)-2-benzyl-8-(p-tolylsulphonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

There total 3 articles about dimethyl (2S,3aR,8aS)-2-benzyl-8-(p-tolylsulphonyl)-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: 71.0%

benzyl bromide (100-39-0) + dimethyl (2S,3aR,8aS)-8-p-tolylsulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (127628-10-8) → dimethyl (2S,3aR,8aS)-2-benzyl-8-(p-tolylsulphonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (127628-12-0)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; 1.) -78 deg C;

DOI:10.1039/c39890001418

Reference yield:

N-(methoxycarbonyl)-L-tryptophan methyl ester (66377-68-2,79631-04-2,58635-46-4) → dimethyl (2S,3aR,8aS)-2-benzyl-8-(p-tolylsulphonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (127628-12-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / 85percent phosphoric acid

2: 85 percent / pyridine

3: 71 percent / 1.) lithium di-isopropylamide / tetrahydrofuran / 1.) -78 deg C

With pyridine; phosphoric acid; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1039/c39890001418

Reference yield:

L-(2β,3aα,8aα)-1,2,3,3a,8,8a-hexahydro-1,2-dimethoxycarbonylpyrrolo<2,3-b>indole (79465-82-0) → dimethyl (2S,3aR,8aS)-2-benzyl-8-(p-tolylsulphonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate (127628-12-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridine

2: 71 percent / 1.) lithium di-isopropylamide / tetrahydrofuran / 1.) -78 deg C

With pyridine; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1039/c39890001418

upstream raw materials:

benzyl bromide

dimethyl (2S,3aR,8aS)-8-p-tolylsulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate

N-(methoxycarbonyl)-L-tryptophan methyl ester

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

Downstream raw materials:

(αS)-α-benzyl-N_α-methoxycarbonyl-1-(p-tolylsulphonyl)tryptophan methyl ester

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