(2S,3S,4S)-2-Benzyloxycarbonylamino-4-hydroxy-3-methoxy-pentanedioic acid dimethyl ester

Base Information

Chemical Name:(2S,3S,4S)-2-Benzyloxycarbonylamino-4-hydroxy-3-methoxy-pentanedioic acid dimethyl ester
CAS No.:175656-11-8
Molecular Formula:C₁₆H₂₁NO₈
Molecular Weight:355.345
Hs Code.:

Synonyms:(2S,3S,4S)-2-Benzyloxycarbonylamino-4-hydroxy-3-methoxy-pentanedioic acid dimethyl ester

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Chemical Property of (2S,3S,4S)-2-Benzyloxycarbonylamino-4-hydroxy-3-methoxy-pentanedioic acid dimethyl ester

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Technology Process of (2S,3S,4S)-2-Benzyloxycarbonylamino-4-hydroxy-3-methoxy-pentanedioic acid dimethyl ester

There total 7 articles about (2S,3S,4S)-2-Benzyloxycarbonylamino-4-hydroxy-3-methoxy-pentanedioic acid dimethyl 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: 83.0%

: 67-56-1
methanol

: 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

: 175656-11-8
(2S,3S,4S)-2-Benzyloxycarbonylamino-4-hydroxy-3-methoxy-pentanedioic acid dimethyl ester

Guidance literature:: With boron trifluoride diethyl etherate; at 20 - 50 ℃; for 4h;
DOI:10.1016/S0040-4039(02)01762-8

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

: 175656-11-8
(2S,3S,4S)-2-Benzyloxycarbonylamino-4-hydroxy-3-methoxy-pentanedioic acid dimethyl ester

Guidance literature:: Multi-step reaction with 3 steps

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

2: boron trifluoride etherate / 0.5 h / Ambient temperature

3: 1.) boron trifluoride etherate, 2.) silica gel / 1.) 50 deg C, 90 min, 2.) heptane, ethyl acetate

With tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; silica gel; 4-methylmorpholine N-oxide; In 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

: 175656-11-8
(2S,3S,4S)-2-Benzyloxycarbonylamino-4-hydroxy-3-methoxy-pentanedioic acid dimethyl ester

Guidance literature:: Multi-step reaction with 4 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: boron trifluoride etherate / 0.5 h / Ambient temperature

4: 1.) boron trifluoride etherate, 2.) silica gel / 1.) 50 deg C, 90 min, 2.) heptane, ethyl acetate

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