(1aR,2aR,4S,5aS,6aS)-Octahydro-1-oxa-5-aza-cyclopropa[f]indene-4,5-dicarboxylic acid 5-benzyl ester 4-methyl ester

Base Information

• Chemical Name: (1aR,2aR,4S,5aS,6aS)-Octahydro-1-oxa-5-aza-cyclopropa[f]indene-4,5-dicarboxylic acid 5-benzyl ester 4-methyl ester
• CAS No.: 477351-59-0
• Molecular Formula: C₁₈H₂₁NO₅
• Molecular Weight: 331.368

Synonyms:(1aR,2aR,4S,5aS,6aS)-Octahydro-1-oxa-5-aza-cyclopropa[f]indene-4,5-dicarboxylic acid 5-benzyl ester 4-methyl ester

Chemical Property of (1aR,2aR,4S,5aS,6aS)-Octahydro-1-oxa-5-aza-cyclopropa[f]indene-4,5-dicarboxylic acid 5-benzyl ester 4-methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (1aR,2aR,4S,5aS,6aS)-Octahydro-1-oxa-5-aza-cyclopropa[f]indene-4,5-dicarboxylic acid 5-benzyl ester 4-methyl ester

There total 2 articles about (1aR,2aR,4S,5aS,6aS)-Octahydro-1-oxa-5-aza-cyclopropa[f]indene-4,5-dicarboxylic acid 5-benzyl ester 4-methyl 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:

(2S,4S,5S)-4,5-Diallyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (477351-56-7) → (1aR,2aR,4S,5aS,6aS)-Octahydro-1-oxa-5-aza-cyclopropa[f]indene-4,5-dicarboxylic acid 5-benzyl ester 4-methyl ester (477351-59-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂

2: m-CPBA / CH₂Cl₂ / 2 h

With 3-chloro-benzenecarboperoxoic acid; Grubbs catalyst first generation; In dichloromethane; 1: Grubbs metathesis reaction;

DOI:10.1021/ja0208153

Reference yield:

(2S,3aS,7aS)-2,3,3a,4,7,7a-Hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (477351-57-8) → (1aR,2aR,4S,5aS,6aS)-Octahydro-1-oxa-5-aza-cyclopropa[f]indene-4,5-dicarboxylic acid 5-benzyl ester 4-methyl ester (477351-59-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 2h;

DOI:10.1021/ja0208153

Reference yield:

(1aR,2aR,4S,5aS,6aS)-Octahydro-1-oxa-5-aza-cyclopropa[f]indene-4,5-dicarboxylic acid 5-benzyl ester 4-methyl ester (477351-59-0) → (2S,3aR,5S,6S,7aS)-5,6-Dihydroxy-octahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (477351-61-4)

Guidance literature:

With water; trifluoroacetic acid; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ja0208153

upstream raw materials:

(2S,3aS,7aS)-2,3,3a,4,7,7a-Hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(2S,4S,5S)-4,5-Diallyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Downstream raw materials:

(2S,3aR,5S,6S,7aS)-5,6-Dihydroxy-octahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(2S,3aR,5S,6S,7aS)-5,6-Bis-methoxymethoxy-octahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester

(2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid

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