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

Base Information

• Chemical Name: (Z)-(3R,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester
• CAS No.: 625109-95-7
• Molecular Formula: C₄₅H₇₀O₅Si₃
• Molecular Weight: 775.304
• Mol file: 625109-95-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (Z)-(3R,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester 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: 87.0%

t-butyldimethylsiyl triflate (69739-34-0) + phenyl (3R,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate (625109-71-9) → (Z)-(3R,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester (625109-95-7)

Guidance literature:

With 2,6-dimethylpyridine; at 20 ℃; for 1h;

DOI:10.1021/jo034901c

Reference yield: 80.0%

(Z)-(3R,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester (625109-95-7) → (Z)-(3R,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-en-1-ol (625109-96-8)

Guidance literature:

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

DOI:10.1021/jo034901c

Reference yield:

(Z)-(3R,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-enoic acid phenyl ester (625109-95-7) → ethyl (2S,3R,5R,6Z,8S,9S,10S)-2-bromo-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenoate (625109-82-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

2.1: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

3.1: BH₃*THF / CH₂Cl₂; tetrahydrofuran / 1 h / 0 - 20 °C

3.2: CH₂Cl₂; tetrahydrofuran / 16 h / -78 °C

4.1: 80 percent / P₂O₅ / CHCl₃ / 3 h / 20 °C

With borane-THF; oxalyl dichloride; phosphorus pentoxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; chloroform; 2.1: Swern oxidation;

DOI:10.1021/jo034901c

upstream raw materials:

t-butyldimethylsiyl triflate

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

Downstream raw materials:

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

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

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

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