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

Base Information

• Chemical Name: 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
• CAS No.: 475051-63-9
• Molecular Formula: C₃₉H₆₁BrO₆Si₂
• Molecular Weight: 761.985
• Mol file: 475051-63-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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: 86.0%

Dimethoxymethane (109-87-5) + (3S,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal (475051-50-4) → 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)

Guidance literature:

With phosphorus pentoxide; In chloroform; at 20 ℃; for 3h;

DOI:10.1021/jo034901c

Reference yield: 80.0%

Dimethoxymethane (109-87-5) + (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 (475051-51-5) → 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)

Guidance literature:

With phosphorus pentoxide; In chloroform; at 20 ℃; for 1h;

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

Reference yield:

phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate (475051-49-1) → 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)

Guidance literature:

Multi-step reaction with 4 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

4: 86 percent / P₂O₅ / CHCl₃ / 3 h / 20 °C

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

DOI:10.1021/jo034901c

upstream raw materials:

Dimethoxymethane

(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

(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

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

(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