(Z)-(2R,3S,5S,8S,9S,10S)-2-Bromo-9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-undec-6-enoic acid ethyl ester

Base Information

Chemical Name:(Z)-(2R,3S,5S,8S,9S,10S)-2-Bromo-9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-undec-6-enoic acid ethyl ester
CAS No.:625109-75-3
Molecular Formula:C₄₆H₆₉BrO₇Si₂
Molecular Weight:870.125
Hs Code.:

(Z)-(2R,3S,5S,8S,9S,10S)-2-Bromo-9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-undec-6-enoic acid ethyl ester

Synonyms:(Z)-(2R,3S,5S,8S,9S,10S)-2-Bromo-9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-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-9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-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-9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-undec-6-enoic acid ethyl ester

There total 5 articles about (Z)-(2R,3S,5S,8S,9S,10S)-2-Bromo-9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-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: 89.0%

: 68005-71-0
N-((4-methylphenyl)sulfonyl)-D-valine

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

: 625109-74-2
(Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enal

: 625109-75-3
(Z)-(2R,3S,5S,8S,9S,10S)-2-Bromo-9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-undec-6-enoic acid ethyl ester

Guidance literature:: N-((4-methylphenyl)sulfonyl)-D-valine; With borane-THF; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 1h;

2-bromo-1-ethoxy-2-methyl-1-trimethylsilyoxyethene; (Z)-(3S,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enal; In tetrahydrofuran; dichloromethane; at -78 ℃;
DOI:10.1021/jo034901c

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 625109-75-3
(Z)-(2R,3S,5S,8S,9S,10S)-2-Bromo-9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-undec-6-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / TfOH / 20 °C

2.1: 74 percent / DIBALH / 2 h / -78 °C

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

3.2: 89 percent / CH₂Cl₂; tetrahydrofuran / -78 °C

With borane-THF; trifluorormethanesulfonic acid; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation;
DOI:10.1021/jo034901c

Reference yield:

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

: 625109-75-3
(Z)-(2R,3S,5S,8S,9S,10S)-2-Bromo-9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,8,10-trimethyl-undec-6-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / TfOH / 20 °C

2.1: 74 percent / DIBALH / 2 h / -78 °C

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

3.2: 89 percent / CH₂Cl₂; tetrahydrofuran / -78 °C

With borane-THF; trifluorormethanesulfonic acid; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation;
DOI:10.1021/jo034901c