(2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate

Base Information

• Chemical Name: (2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate
• CAS No.: 1352575-56-4
• Molecular Formula: C₄₁H₄₀N₄O₇
• Molecular Weight: 700.791

Synonyms:(2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate

Chemical Property of (2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate

There total 7 articles about (2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-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: 98.0%

(2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate (1352575-50-8) + benzyl chloroformate (501-53-1,94274-21-2) → (2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate (1352575-56-4)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In dichloromethane; at 23 ℃; for 5h; Inert atmosphere;

DOI:10.1002/anie.201103145

Reference yield:

(2R,3aS,8aS)-8-benzyl 1-tert-butyl 2-methyl 3a-bromo-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate (1352575-47-3) → (2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate (1352575-56-4)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran; water / 96 h / 23 °C / Inert atmosphere

2: tris(bipyridine)ruthenium(II) dichloride hexahydrate; tributyl-amine / N,N-dimethyl-formamide / 12 h / 30 °C / Inert atmosphere; Irradiation

3: Wilkinson's catalyst / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / 140 °C / Inert atmosphere

4: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / dichloromethane / 5 h / 23 °C / Inert atmosphere

With Wilkinson's catalyst; tris(bipyridine)ruthenium(II) dichloride hexahydrate; tributyl-amine; tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/anie.201103145

Reference yield:

(2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(2-formyl-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate (1352575-49-5) → (2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate (1352575-56-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Wilkinson's catalyst / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / 140 °C / Inert atmosphere

2: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / dichloromethane / 5 h / 23 °C / Inert atmosphere

With Wilkinson's catalyst; tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane;

DOI:10.1002/anie.201103145

upstream raw materials:

(R)-benzyl 3-(2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)-1H-indole-1-carboxylate

(2R,3aS,8aS)-8-benzyl 1-tert-butyl 2-methyl 3a-bromo-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate

(2R,3aS,8aS)-8-benzyl 1-tert-butyl 3a-bromo-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate

(2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(2-formyl-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate

Downstream raw materials:

(3aR,8aS)-benzyl 3a-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-8(8aH)-carboxylate

(5aS,10bR)-benzyl 10b-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-methyl-1,3,4-trioxo-3,4,5a,10b-tetrahydro-1H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-6(2H)-carboxylate

C₃₆H₃₂N₄O₅

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