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

Base Information

• Chemical Name: (2S,3S,5S,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal
• CAS No.: 475051-53-7
• Molecular Formula: C₃₇H₅₈O₅Si₂
• Molecular Weight: 639.036
• Mol file: 475051-53-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (2S,3S,5S,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal 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: 90.0%

(S)-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-propionic acid ethyl ester (475051-52-6) → (2S,3S,5S,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal (475051-53-7)

Guidance literature:

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

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

Reference yield: 88.0%

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 (475051-63-9) → (2S,3S,5S,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal (475051-53-7)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 2h;

DOI:10.1021/jo034901c

Reference yield:

(3S,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal (475051-50-4) → (2S,3S,5S,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal (475051-53-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / P₂O₅ / CHCl₃ / 3 h / 20 °C

2: 88 percent / DIBAL / CH₂Cl₂; toluene / 2 h / -78 °C

With phosphorus pentoxide; diisobutylaluminium hydride; In dichloromethane; chloroform; toluene;

DOI:10.1021/jo034901c

upstream raw materials:

(S)-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-propionic 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

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

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

Downstream raw materials:

(2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester