5-[4-((1R,4R,5R,6S)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-4-hydroxy-4,5-dimethyl-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester

Base Information

• Chemical Name: 5-[4-((1R,4R,5R,6S)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-4-hydroxy-4,5-dimethyl-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester
• CAS No.: 131194-88-2
• Molecular Formula: C₅₁H₄₉N₃O₉
• Molecular Weight: 847.965

Synonyms:

Chemical Property of 5-[4-((1R,4R,5R,6S)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-4-hydroxy-4,5-dimethyl-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester

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Technology Process of 5-[4-((1R,4R,5R,6S)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-4-hydroxy-4,5-dimethyl-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester

There total 3 articles about 5-[4-((1R,4R,5R,6S)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-4-hydroxy-4,5-dimethyl-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester 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: 47.0%

methyllithium (917-54-4) + 5-[4-((1S,5S,6R)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-5-methyl-4-oxo-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester (131213-35-9) → 5-[4-((1R,4R,5R,6S)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-4-hydroxy-4,5-dimethyl-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester (131194-88-2)

Guidance literature:

In tetrahydrofuran; diethyl ether; 1a) -78 deg C, 30 min, 1b) 0 deg C, 1.5 h;

DOI:10.1021/jo00001a023

Reference yield:

C35H35N3O8 (124857-19-8) → 5-[4-((1R,4R,5R,6S)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-4-hydroxy-4,5-dimethyl-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester (131194-88-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / benzene / 3.5 h / Heating

2: 47 percent / tetrahydrofuran; diethyl ether / 1a) -78 deg C, 30 min, 1b) 0 deg C, 1.5 h

In tetrahydrofuran; diethyl ether; benzene;

DOI:10.1021/jo00001a023

Reference yield:

diphenylcyclopropenone (886-38-4) → 5-[4-((1R,4R,5R,6S)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-4-hydroxy-4,5-dimethyl-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester (131194-88-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / benzene / 3.5 h / Heating

2: 47 percent / tetrahydrofuran; diethyl ether / 1a) -78 deg C, 30 min, 1b) 0 deg C, 1.5 h

In tetrahydrofuran; diethyl ether; benzene;

DOI:10.1021/jo00001a023

upstream raw materials:

methyllithium

5-[4-((1S,5S,6R)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-5-methyl-4-oxo-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester

C₃₅H₃₅N₃O₈

diphenylcyclopropenone

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