(2R,3S,4S)-4-(1-Hydroxymethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

Chemical Name:(2R,3S,4S)-4-(1-Hydroxymethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
CAS No.:120211-86-1
Molecular Formula:C₂₀H₂₅NO₇
Molecular Weight:391.421
Hs Code.:

Synonyms:(2R,3S,4S)-4-(1-Hydroxymethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Chemical Property of (2R,3S,4S)-4-(1-Hydroxymethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Technology Process of (2R,3S,4S)-4-(1-Hydroxymethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 1 articles about (2R,3S,4S)-4-(1-Hydroxymethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-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: 97.0%

: 120211-85-0
(2R,3S,4S)-4-(1-Formyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 120211-86-1
(2R,3S,4S)-4-(1-Hydroxymethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃;
DOI:10.1039/c39880001204

Reference yield: 67.0%

: 120211-86-1
(2R,3S,4S)-4-(1-Hydroxymethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 120229-01-8
(2R,3S,4S)-4-(1-Chloromethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: With dmap; triethylamine; p-toluenesulfonyl chloride; In dichloromethane; Ambient temperature;
DOI:10.1039/c39880001204

Reference yield:

: 120211-86-1
(2R,3S,4S)-4-(1-Hydroxymethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 73903-33-0
(2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 67 percent / toluene-p-sulfonyl chloride, triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature

2: 80 percent / tri-n-butyltin hydride, azobisisobutyronitrile / benzene / 3 h / Heating

3: NaH, 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 24 h / Ambient temperature

4: aq. NaOH / Heating

With dmap; sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; In dichloromethane; benzene;
DOI:10.1039/c39880001204