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

Base Information

• Chemical Name: (+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid
• CAS No.: 171256-40-9
• Molecular Formula: C₁₉H₁₈N₂O₆S
• Molecular Weight: 402.428
• Mol file: 171256-40-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid 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: 100.0%

dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate (136057-11-9) → (+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid (171256-40-9)

Guidance literature:

dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate; With water; lithium hydroxide; In tetrahydrofuran; for 2.5h; Reflux;

With hydrogenchloride; pH=5;

DOI:10.1002/ejoc.201101057

Reference yield:

(+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-2-<2-(methoxycarbonyl)vinyl>-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 (171256-40-9)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; for 10h; Yield given; Ambient temperature;

DOI:10.1021/jo00124a055

Reference yield:

(S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) → (+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid (171256-40-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 2 h / 20 °C

2.1: phosphoric acid / 3 h / 20 °C / Inert atmosphere

3.1: pyridine / 0 - 20 °C

4.1: water; lithium hydroxide / tetrahydrofuran / 2.5 h / Reflux

4.2: pH 5

With pyridine; phosphoric acid; water; triethylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.201101057

upstream raw materials:

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

(S)-tryptophan methyl ester hydrochloride

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:

(2R,3aR,8aS)-8-benzenesulfonyl-2-phenylselenyl-3,3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester

(2R,3aR,8aS)-2-allyl-8-benzenesulfonyl-3,3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester

C₂₃H₂₆N₂O₆S

C₄₈H₅₉N₅O₁₁S