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

Base Information

• Chemical Name: (3S,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal
• CAS No.: 475051-50-4
• Molecular Formula: C₃₉H₆₆O₄Si₃
• Molecular Weight: 683.207
• Mol file: 475051-50-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (3S,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal 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: 93.0%

(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) → (3S,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal (475051-50-4)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃;

DOI:10.1021/jo034901c

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (3S,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal (475051-50-4)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 93 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

With 2,6-dimethylpyridine; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; 3: Swern oxidation;

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) → (3S,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal (475051-50-4)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 93 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

With 2,6-dimethylpyridine; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; 3: Swern oxidation;

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-en-1-ol

t-butyldimethylsiyl triflate

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

(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

Downstream raw materials:

(Z)-(2R,3S,5S,8S,9S,10S)-2-Bromo-5,9-bis-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,8,10-trimethyl-undec-6-enoic acid ethyl ester

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

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