(-)-(2R,3R,4S)-2-benzyloxy-3-(tert-butoxycarbonyl)amino-4-[tert-butyl(dimethyl)silyloxy]-4-cyanobutyl methanesulfonate

Base Information

Chemical Name:(-)-(2R,3R,4S)-2-benzyloxy-3-(tert-butoxycarbonyl)amino-4-[tert-butyl(dimethyl)silyloxy]-4-cyanobutyl methanesulfonate
CAS No.:956428-80-1
Molecular Formula:C₂₄H₄₀N₂O₇SSi
Molecular Weight:528.742
Hs Code.:

Synonyms:(-)-(2R,3R,4S)-2-benzyloxy-3-(tert-butoxycarbonyl)amino-4-[tert-butyl(dimethyl)silyloxy]-4-cyanobutyl methanesulfonate

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Chemical Property of (-)-(2R,3R,4S)-2-benzyloxy-3-(tert-butoxycarbonyl)amino-4-[tert-butyl(dimethyl)silyloxy]-4-cyanobutyl methanesulfonate

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Technology Process of (-)-(2R,3R,4S)-2-benzyloxy-3-(tert-butoxycarbonyl)amino-4-[tert-butyl(dimethyl)silyloxy]-4-cyanobutyl methanesulfonate

There total 7 articles about (-)-(2R,3R,4S)-2-benzyloxy-3-(tert-butoxycarbonyl)amino-4-[tert-butyl(dimethyl)silyloxy]-4-cyanobutyl methanesulfonate 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: 68.0%

: 956428-78-7
tert-butyl (-)-(1R,2R)-2-benzyloxy-1-[(S)-[tert-butyl(dimethyl)silyloxy](cyano)methyl]-3-hydroxypropylcarbamate

: 124-63-0
methanesulfonyl chloride

: 956428-80-1
(-)-(2R,3R,4S)-2-benzyloxy-3-(tert-butoxycarbonyl)amino-4-[tert-butyl(dimethyl)silyloxy]-4-cyanobutyl methanesulfonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1021/jo701452a

Reference yield:

: 956428-53-8
(+)-(2S)-[(2R,3R)-3-benzyloxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl][tert-butyl(dimethyl)silyloxy]acetonitrile

: 956428-80-1
(-)-(2R,3R,4S)-2-benzyloxy-3-(tert-butoxycarbonyl)amino-4-[tert-butyl(dimethyl)silyloxy]-4-cyanobutyl methanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1: 74 percent / lithium borohydride / diethyl ether / 0 - 20 °C

2: (diacetoxyiodo)benzene; acetic acid / methanol / 0.5 h / 20 °C

3: 76 mg / methanol; H₂O; CH₂Cl₂ / 20 °C

4: 68 percent / triethylamine; DMAP / CH₂Cl₂ / 20 °C

With dmap; lithium borohydride; [bis(acetoxy)iodo]benzene; acetic acid; triethylamine; In methanol; diethyl ether; dichloromethane; water;
DOI:10.1021/jo701452a

Reference yield:

: 956428-70-9
(+)-(2S,3R,4R)-4-benzyloxy-2-[tert-butyl(dimethyl)silyloxy]-5-hydroxy-3-[(4-methoxyphenyl)amino]pentanenitrile

: 956428-80-1
(-)-(2R,3R,4S)-2-benzyloxy-3-(tert-butoxycarbonyl)amino-4-[tert-butyl(dimethyl)silyloxy]-4-cyanobutyl methanesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1: (diacetoxyiodo)benzene; acetic acid / methanol / 0.5 h / 20 °C

2: 76 mg / methanol; H₂O; CH₂Cl₂ / 20 °C

3: 68 percent / triethylamine; DMAP / CH₂Cl₂ / 20 °C

With dmap; [bis(acetoxy)iodo]benzene; acetic acid; triethylamine; In methanol; dichloromethane; water;
DOI:10.1021/jo701452a