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

Base Information

• Chemical Name: (+)-(2S,3aR,8aS)-3a-Allyl-1,2-bis(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole
• CAS No.: 157989-22-5
• Molecular Formula: C₂₃H₂₄N₂O₆S
• Molecular Weight: 456.519
• Mol file: 157989-22-5.mol

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

Chemical Property of (+)-(2S,3aR,8aS)-3a-Allyl-1,2-bis(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2S,3aR,8aS)-3a-Allyl-1,2-bis(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole

There total 2 articles about (+)-(2S,3aR,8aS)-3a-Allyl-1,2-bis(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole 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%

allyltributylstanane (24850-33-7) + (+)-(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) → (+)-(2S,3aR,8aS)-3a-Allyl-1,2-bis(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole (157989-22-5)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In benzene; for 18h; Heating;

DOI:10.1021/jo00098a011

Reference yield:

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)-3a-Allyl-1,2-bis(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole (157989-22-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / AIBN, NBS / CCl₄ / 0.5 h / Heating

2: 80 percent / AIBN / benzene / 18 h / Heating

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; benzene;

DOI:10.1021/jo00098a011

Reference yield: 99.0%

(+)-(2S,3aR,8aS)-3a-Allyl-1,2-bis(methoxycarbonyl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole (157989-22-5) → (+)-(2S,3aR,8aS)-3a-Allyl-1-methoxycarbonyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2.3-b>indole-2-carboxylic acid

Guidance literature:

With potassium hydroxide; In methanol; water; for 4h; Ambient temperature;

DOI:10.1016/0040-4020(95)00307-T

upstream raw materials:

allyltributylstanane

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

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

Downstream raw materials:

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

(+)-(3aR,8aS)-3a-(3-Methyl-2-buten-1-yl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole

(+)-(3aR,8aS)-1-Methyl-3a-(3-methyl-2-buten-1-yl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole

(+)-(3aR,8aS)-1-(Methoxycarbonyl)-3a-(3-methyl-2-buten-1-yl)-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole