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

Base Information

• Chemical Name: (+)-(2S,3R,4R)-4-benzyloxy-2-[tert-butyl(dimethyl)silyloxy]-5-hydroxy-3-[(4-methoxyphenyl)amino]pentanenitrile
• CAS No.: 956428-70-9
• Molecular Formula: C₂₅H₃₆N₂O₄Si
• Molecular Weight: 456.657
• Mol file: 956428-70-9.mol

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

Chemical Property of (+)-(2S,3R,4R)-4-benzyloxy-2-[tert-butyl(dimethyl)silyloxy]-5-hydroxy-3-[(4-methoxyphenyl)amino]pentanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2S,3R,4R)-4-benzyloxy-2-[tert-butyl(dimethyl)silyloxy]-5-hydroxy-3-[(4-methoxyphenyl)amino]pentanenitrile

There total 4 articles about (+)-(2S,3R,4R)-4-benzyloxy-2-[tert-butyl(dimethyl)silyloxy]-5-hydroxy-3-[(4-methoxyphenyl)amino]pentanenitrile 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: 74.0%

(+)-(2S)-[(2R,3R)-3-benzyloxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl][tert-butyl(dimethyl)silyloxy]acetonitrile (956428-53-8) → (+)-(2S,3R,4R)-4-benzyloxy-2-[tert-butyl(dimethyl)silyloxy]-5-hydroxy-3-[(4-methoxyphenyl)amino]pentanenitrile (956428-70-9)

Guidance literature:

With lithium borohydride; In diethyl ether; at 0 - 20 ℃;

DOI:10.1021/jo701452a

Reference yield:

(+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone (149818-33-7) → (+)-(2S,3R,4R)-4-benzyloxy-2-[tert-butyl(dimethyl)silyloxy]-5-hydroxy-3-[(4-methoxyphenyl)amino]pentanenitrile (956428-70-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / sodium carbonate / acetonitrile / 1.5 h / 20 °C

2: 74 percent / lithium borohydride / diethyl ether / 0 - 20 °C

With lithium borohydride; sodium carbonate; In diethyl ether; acetonitrile;

DOI:10.1021/jo701452a

Reference yield:

(+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone (148968-08-5) → (+)-(2S,3R,4R)-4-benzyloxy-2-[tert-butyl(dimethyl)silyloxy]-5-hydroxy-3-[(4-methoxyphenyl)amino]pentanenitrile (956428-70-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / sodium carbonate / acetonitrile / 1.5 h / 20 °C

2: 74 percent / lithium borohydride / diethyl ether / 0 - 20 °C

With lithium borohydride; sodium carbonate; In diethyl ether; acetonitrile;

DOI:10.1021/jo701452a

upstream raw materials:

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

(+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone

(+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone

(3R,4S)-3-(Benzyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-1-(4-methoxyphenyl)azetidin-2-one

Downstream raw materials:

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

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