(2S,3S,4S)-3-Benzyloxy-2-benzyloxycarbonylamino-4-hydroxy-pentanedioic acid 1-benzyl ester 5-methyl ester

Base Information

Chemical Name:(2S,3S,4S)-3-Benzyloxy-2-benzyloxycarbonylamino-4-hydroxy-pentanedioic acid 1-benzyl ester 5-methyl ester
CAS No.:175656-15-2
Molecular Formula:C₂₈H₂₉NO₈
Molecular Weight:507.54
Hs Code.:

Synonyms:(2S,3S,4S)-3-Benzyloxy-2-benzyloxycarbonylamino-4-hydroxy-pentanedioic acid 1-benzyl ester 5-methyl ester

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Chemical Property of (2S,3S,4S)-3-Benzyloxy-2-benzyloxycarbonylamino-4-hydroxy-pentanedioic acid 1-benzyl ester 5-methyl ester

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Technology Process of (2S,3S,4S)-3-Benzyloxy-2-benzyloxycarbonylamino-4-hydroxy-pentanedioic acid 1-benzyl ester 5-methyl ester

There total 4 articles about (2S,3S,4S)-3-Benzyloxy-2-benzyloxycarbonylamino-4-hydroxy-pentanedioic acid 1-benzyl ester 5-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: 39.0%

: 175656-08-3
(1R,2S,5S)-4-Oxo-3-oxa-6-aza-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester

: 100-51-6,185532-71-2
benzyl alcohol

: 175656-15-2
(2S,3S,4S)-3-Benzyloxy-2-benzyloxycarbonylamino-4-hydroxy-pentanedioic acid 1-benzyl ester 5-methyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In chloroform; 1.) room temperature, 30 min, 2.) 60 deg C, 2 h;
DOI:10.1021/jo951983z

Reference yield:

: (1R,2S,4R,5S)-4-Hydroxy-3-oxa-6-aza-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester

: 175656-15-2
(2S,3S,4S)-3-Benzyloxy-2-benzyloxycarbonylamino-4-hydroxy-pentanedioic acid 1-benzyl ester 5-methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 77 percent / tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide, 4A molecular sieves / acetonitrile / 4 h

2: 39 percent / boron trifluoride etherate / CHCl₃ / 1.) room temperature, 30 min, 2.) 60 deg C, 2 h

With tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; 4-methylmorpholine N-oxide; In chloroform; acetonitrile;
DOI:10.1021/jo951983z

Reference yield:

: 175656-06-1
(1R,2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-oxa-6-aza-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester

: 175656-15-2
(2S,3S,4S)-3-Benzyloxy-2-benzyloxycarbonylamino-4-hydroxy-pentanedioic acid 1-benzyl ester 5-methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / tetrabutylammonium fluoride / CH₂Cl₂ / 1.5 h / -65 - 20 °C

2: 77 percent / tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide, 4A molecular sieves / acetonitrile / 4 h

3: 39 percent / boron trifluoride etherate / CHCl₃ / 1.) room temperature, 30 min, 2.) 60 deg C, 2 h

With tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; In dichloromethane; chloroform; acetonitrile;
DOI:10.1021/jo951983z