(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

Base Information

Chemical Name:(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
CAS No.:475051-51-5
Molecular Formula:C₄₄H₇₅BrO₆Si₃
Molecular Weight:864.236
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 5 articles about (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 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:

: 69739-34-0
t-butyldimethylsiyl triflate

: 475051-51-5
(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

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: 90 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / -78 - 0 °C

4: BH₃*THF / chiral borane from L-TsVal / -78 °C

With 2,6-dimethylpyridine; borane-THF; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; chiral borane from L-TsVal; In dichloromethane; 3: Swern oxidation;
DOI:10.1016/S0040-4039(02)01389-8

Reference yield:

: 475051-61-7
(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

: 475051-51-5
(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

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

2: 90 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / -78 - 0 °C

3: BH₃*THF / chiral borane from L-TsVal / -78 °C

With borane-THF; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; chiral borane from L-TsVal; In dichloromethane; 2: Swern oxidation;
DOI:10.1016/S0040-4039(02)01389-8

Reference yield:

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

: 475051-51-5
(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

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: 90 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / -78 - 0 °C

4: BH₃*THF / chiral borane from L-TsVal / -78 °C

With 2,6-dimethylpyridine; borane-THF; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; chiral borane from L-TsVal; In dichloromethane; 3: Swern oxidation;
DOI:10.1016/S0040-4039(02)01389-8