(Z)-(3S,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-en-1-ol

Base Information

• Chemical Name: (Z)-(3S,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-en-1-ol
• CAS No.: 475051-62-8
• Molecular Formula: C₃₉H₆₈O₄Si₃
• Molecular Weight: 685.223
• Mol file: 475051-62-8.mol

Synonyms:(Z)-(3S,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-en-1-ol

Chemical Property of (Z)-(3S,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(3S,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-en-1-ol

There total 3 articles about (Z)-(3S,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-en-1-ol 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: 80.0%

(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 (475051-61-7) → (Z)-(3S,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-en-1-ol (475051-62-8)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 3h;

DOI:10.1016/S0040-4039(02)01389-8 DOI:10.1021/jo034901c

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (Z)-(3S,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-en-1-ol (475051-62-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / 2,6-lutidine / 1 h / 20 °C

2: 80 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1016/S0040-4039(02)01389-8 DOI:10.1021/jo034901c

Reference yield:

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)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-en-1-ol (475051-62-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / 2,6-lutidine / 1 h / 20 °C

2: 80 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1016/S0040-4039(02)01389-8 DOI:10.1021/jo034901c

upstream 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

t-butyldimethylsiyl triflate

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

Downstream raw materials:

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

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

ethyl (2R,3S,5S,6Z,8S,9S,10S)-2-bromo-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenoate

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