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

Base Information

• Chemical Name: tert-butyl (-)-(1R,2R)-2-benzyloxy-1-[(S)-[tert-butyl(dimethyl)silyloxy](cyano)methyl]-3-hydroxypropylcarbamate
• CAS No.: 956428-78-7
• Molecular Formula: C₂₃H₃₈N₂O₅Si
• Molecular Weight: 450.651
• Mol file: 956428-78-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about tert-butyl (-)-(1R,2R)-2-benzyloxy-1-[(S)-[tert-butyl(dimethyl)silyloxy](cyano)methyl]-3-hydroxypropylcarbamate 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:

(+)-(2S)-[(2R,3R)-3-benzyloxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl][tert-butyl(dimethyl)silyloxy]acetonitrile (956428-53-8) → tert-butyl (-)-(1R,2R)-2-benzyloxy-1-[(S)-[tert-butyl(dimethyl)silyloxy](cyano)methyl]-3-hydroxypropylcarbamate (956428-78-7)

Guidance literature:

Multi-step reaction with 3 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

With lithium borohydride; [bis(acetoxy)iodo]benzene; acetic acid; In methanol; diethyl ether; dichloromethane; water;

DOI:10.1021/jo701452a

Reference yield:

(+)-(2S,3R,4R)-4-benzyloxy-2-[tert-butyl(dimethyl)silyloxy]-5-hydroxy-3-[(4-methoxyphenyl)amino]pentanenitrile (956428-70-9) → tert-butyl (-)-(1R,2R)-2-benzyloxy-1-[(S)-[tert-butyl(dimethyl)silyloxy](cyano)methyl]-3-hydroxypropylcarbamate (956428-78-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With [bis(acetoxy)iodo]benzene; acetic acid; In methanol; dichloromethane; water;

DOI:10.1021/jo701452a

Reference yield:

(+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone (149818-33-7) → tert-butyl (-)-(1R,2R)-2-benzyloxy-1-[(S)-[tert-butyl(dimethyl)silyloxy](cyano)methyl]-3-hydroxypropylcarbamate (956428-78-7)

Guidance literature:

Multi-step reaction with 5 steps

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

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

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

4: 76 mg / methanol; H₂O; CH₂Cl₂ / 20 °C

With lithium borohydride; [bis(acetoxy)iodo]benzene; sodium carbonate; acetic acid; In methanol; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1021/jo701452a

upstream raw materials:

di-tert-butyl dicarbonate

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

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

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

Downstream raw materials:

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