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

Base Information

Chemical Name:ethyl (2S,3R,5R,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-hydroxy-2,8,10-trimethyl-6-undecenoate
CAS No.:625109-81-1
Molecular Formula:C₄₄H₇₅BrO₆Si₃
Molecular Weight:864.236
Hs Code.:

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

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Chemical Property of ethyl (2S,3R,5R,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-hydroxy-2,8,10-trimethyl-6-undecenoate

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Technology Process of ethyl (2S,3R,5R,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-hydroxy-2,8,10-trimethyl-6-undecenoate

There total 5 articles about ethyl (2S,3R,5R,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-hydroxy-2,8,10-trimethyl-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:

: 17360-25-7,32013-47-1,68005-71-0
N-(p-toluenesulfonyl)-L-valine

: 153645-08-0
2-bromo-1-ethoxy-2-methyl-1-trimethylsilyoxyethene

: 625109-80-0
(3R,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal

: 625109-81-1
ethyl (2S,3R,5R,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-hydroxy-2,8,10-trimethyl-6-undecenoate

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

Guidance literature:: N-(p-toluenesulfonyl)-L-valine; With borane-THF; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 1h;

2-bromo-1-ethoxy-2-methyl-1-trimethylsilyoxyethene; (3R,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal; In tetrahydrofuran; dichloromethane; at -78 ℃; for 16h;
DOI:10.1021/jo034901c

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 625109-81-1
ethyl (2S,3R,5R,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-hydroxy-2,8,10-trimethyl-6-undecenoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 87 percent / 2,6-lutidine / 1 h / 20 °C

2.1: 80 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

3.1: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

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

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

With 2,6-dimethylpyridine; borane-THF; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation;
DOI:10.1021/jo034901c

Reference yield:

: 625109-71-9
phenyl (3R,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate

: 625109-81-1
ethyl (2S,3R,5R,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-hydroxy-2,8,10-trimethyl-6-undecenoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 87 percent / 2,6-lutidine / 1 h / 20 °C

2.1: 80 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

3.1: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

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

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

With 2,6-dimethylpyridine; borane-THF; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation;
DOI:10.1021/jo034901c