(7S,8R,9S,10S,11S)-11,13-di-(t-butylimethylsilyloxy)-1-(t-butyldiphenylsilyloxy)-9-(p-methoxybenzyloxy)-5,8,10-trimethyltrideca-2,5-dien-7-ol

Base Information

Chemical Name:(7S,8R,9S,10S,11S)-11,13-di-(t-butylimethylsilyloxy)-1-(t-butyldiphenylsilyloxy)-9-(p-methoxybenzyloxy)-5,8,10-trimethyltrideca-2,5-dien-7-ol
CAS No.:669777-03-1
Molecular Formula:C₅₂H₈₄O₆Si₃
Molecular Weight:889.492
Hs Code.:

Synonyms:(7S,8R,9S,10S,11S)-11,13-di-(t-butylimethylsilyloxy)-1-(t-butyldiphenylsilyloxy)-9-(p-methoxybenzyloxy)-5,8,10-trimethyltrideca-2,5-dien-7-ol

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Chemical Property of (7S,8R,9S,10S,11S)-11,13-di-(t-butylimethylsilyloxy)-1-(t-butyldiphenylsilyloxy)-9-(p-methoxybenzyloxy)-5,8,10-trimethyltrideca-2,5-dien-7-ol

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Technology Process of (7S,8R,9S,10S,11S)-11,13-di-(t-butylimethylsilyloxy)-1-(t-butyldiphenylsilyloxy)-9-(p-methoxybenzyloxy)-5,8,10-trimethyltrideca-2,5-dien-7-ol

There total 6 articles about (7S,8R,9S,10S,11S)-11,13-di-(t-butylimethylsilyloxy)-1-(t-butyldiphenylsilyloxy)-9-(p-methoxybenzyloxy)-5,8,10-trimethyltrideca-2,5-dien-7-ol 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:

: 669776-99-2
(2E,5E)-1-(t-butyldiphenylsiloxy)-6-iodo-5-methyl-2,5-hexadiene

: (2S,3R,4S,5S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-heptanal

: 669777-03-1
(7S,8R,9S,10S,11S)-11,13-di-(t-butylimethylsilyloxy)-1-(t-butyldiphenylsilyloxy)-9-(p-methoxybenzyloxy)-5,8,10-trimethyltrideca-2,5-dien-7-ol

: 669777-04-2
(7R,8R,9S,10S,11S)-11,13-di-(t-butylimethylsilyloxy)-1-(t-butyldiphenylsilyloxy)-9-(p-methoxybenzyloxy)-5,8,10-trimethyltrideca-2,5-dien-7-ol

Guidance literature:: (2E,5E)-1-(t-butyldiphenylsiloxy)-6-iodo-5-methyl-2,5-hexadiene; With tert.-butyl lithium; In diethyl ether; pentane; for 1h; cooling;

With magnesium bromide; In diethyl ether; pentane; for 1h;

(2S,3R,4S,5S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-heptanal; In diethyl ether; pentane; at -78 - 20 ℃;
DOI:10.1021/ol0363568

Reference yield:

: 78592-73-1
(E)-4-iodo-3-methylbut-3-en-1-ol

: 669777-03-1
(7S,8R,9S,10S,11S)-11,13-di-(t-butylimethylsilyloxy)-1-(t-butyldiphenylsilyloxy)-9-(p-methoxybenzyloxy)-5,8,10-trimethyltrideca-2,5-dien-7-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydrogen carbonate; Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

2.1: 2.13 g / CH₂Cl₂ / 3 h

3.1: 92 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 - 20 °C

4.1: 97 percent / imidazole / dimethylformamide / 3 h / 0 - 20 °C

5.1: tert-butyllithium / diethyl ether; pentane / 1 h / cooling

5.2: diethyl ether; pentane / -78 - 20 °C

With 1H-imidazole; tert.-butyl lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol0363568

Reference yield:

: 669776-98-1
(2E,5E)-6-iodo-5-methyl-2,5-hexadien-1-ol

: 669777-03-1
(7S,8R,9S,10S,11S)-11,13-di-(t-butylimethylsilyloxy)-1-(t-butyldiphenylsilyloxy)-9-(p-methoxybenzyloxy)-5,8,10-trimethyltrideca-2,5-dien-7-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 97 percent / imidazole / dimethylformamide / 3 h / 0 - 20 °C

2.1: tert-butyllithium / diethyl ether; pentane / 1 h / cooling

2.2: diethyl ether; pentane / -78 - 20 °C

With 1H-imidazole; tert.-butyl lithium; In diethyl ether; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol0363568