phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate

Base Information

• Chemical Name: phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate
• CAS No.: 475051-49-1
• Molecular Formula: C₃₉H₅₆O₅Si₂
• Molecular Weight: 661.042
• Mol file: 475051-49-1.mol

Synonyms:phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate

Chemical Property of phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate

There total 2 articles about phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate 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: 89.0%

N-(p-toluenesulfonyl)-L-valine (17360-25-7,32013-47-1,68005-71-0) + 1-phenoxy-1-trimethylsilyloxyethene (111061-31-5) + (4S,5S,6S)-5-(tert-butyldimethylsiloxy)-7-(tert-butyldiphenylsiloxy)-4,6-dimethyl-2-heptenal → phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate (475051-49-1)

Guidance literature:

N-(p-toluenesulfonyl)-L-valine; With borane-THF; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 1h;

1-phenoxy-1-trimethylsilyloxyethene; (4S,5S,6S)-5-(tert-butyldimethylsiloxy)-7-(tert-butyldiphenylsiloxy)-4,6-dimethyl-2-heptenal; In tetrahydrofuran; dichloromethane; at -78 ℃; for 16h;

DOI:10.1021/jo034901c

Reference yield: 86.0%

1-phenoxy-1-trimethylsilyloxyethene (111061-31-5) + (Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enal (475051-48-0) → phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate (475051-49-1)

Guidance literature:

With borane-THF; chiral oxazaborolidinone from D-TsVal; at -78 ℃; for 16h;

DOI:10.1016/S0040-4039(02)01389-8

Reference yield: 88.0%

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) + phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate (475051-49-1) → (Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester (625109-72-0)

Guidance literature:

With trifluorormethanesulfonic acid; at 20 ℃;

DOI:10.1021/jo034901c

upstream raw materials:

1-phenoxy-1-trimethylsilyloxyethene

(Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enal

N-(p-toluenesulfonyl)-L-valine

Downstream raw materials:

(Z)-(3S,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester

(Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester

(2S,3S,5S,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal

(3S,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal