(3R,5S,6E,9Z)-11-(tert-butyldiphenylsilanyloxy)-3,5-dihydroxy-9-methylundeca-6,9-dienoic acid butyl ester

Base Information

Chemical Name:(3R,5S,6E,9Z)-11-(tert-butyldiphenylsilanyloxy)-3,5-dihydroxy-9-methylundeca-6,9-dienoic acid butyl ester
CAS No.:860651-88-3
Molecular Formula:C₃₂H₄₆O₅Si
Molecular Weight:538.8
Hs Code.:

Synonyms:(3R,5S,6E,9Z)-11-(tert-butyldiphenylsilanyloxy)-3,5-dihydroxy-9-methylundeca-6,9-dienoic acid butyl ester

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Chemical Property of (3R,5S,6E,9Z)-11-(tert-butyldiphenylsilanyloxy)-3,5-dihydroxy-9-methylundeca-6,9-dienoic acid butyl ester

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Technology Process of (3R,5S,6E,9Z)-11-(tert-butyldiphenylsilanyloxy)-3,5-dihydroxy-9-methylundeca-6,9-dienoic acid butyl ester

There total 5 articles about (3R,5S,6E,9Z)-11-(tert-butyldiphenylsilanyloxy)-3,5-dihydroxy-9-methylundeca-6,9-dienoic acid butyl 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:

: 860652-02-4
(S,6E,9Z)-11-(tert-butyldiphenylsilanyloxy)-5-hydroxy-9-methyl-3-oxoundeca-6,9-dienoic acid butyl ester

: 860651-88-3
(3R,5S,6E,9Z)-11-(tert-butyldiphenylsilanyloxy)-3,5-dihydroxy-9-methylundeca-6,9-dienoic acid butyl ester

Guidance literature:: With sodium tetrahydroborate; diethyl methoxy borane; In tetrahydrofuran; at -78 ℃; for 18h;
DOI:10.1002/anie.200500564

Reference yield:

: 860651-93-0
(2E,5Z)-7-(tert-butyldiphenylsilanyloxy)-5-methylhepta-2,5-dienal

: 860651-88-3
(3R,5S,6E,9Z)-11-(tert-butyldiphenylsilanyloxy)-3,5-dihydroxy-9-methylundeca-6,9-dienoic acid butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: SiCl₄; chiral Denmark's bisphosphoramide catalyst / CH₂Cl₂ / 18 h / -78 °C

2: 1 h / Heating

3: diethylmethoxyborane; NaBH₄ / tetrahydrofuran / 18 h / -78 °C

With sodium tetrahydroborate; tetrachlorosilane; chiral Denmark's bisphosphoramide catalyst; diethyl methoxy borane; In tetrahydrofuran; dichloromethane;
DOI:10.1002/anie.200500564

Reference yield:

: tert-Butyl-((2Z,5E)-7,7-dimethoxy-3-methyl-hepta-2,5-dienyloxy)-diphenyl-silane

: 860651-88-3
(3R,5S,6E,9Z)-11-(tert-butyldiphenylsilanyloxy)-3,5-dihydroxy-9-methylundeca-6,9-dienoic acid butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 2.95 g / HCO₂H / CH₂Cl₂; CHCl₃ / 1 h / 20 °C

2: SiCl₄; chiral Denmark's bisphosphoramide catalyst / CH₂Cl₂ / 18 h / -78 °C

3: 1 h / Heating

4: diethylmethoxyborane; NaBH₄ / tetrahydrofuran / 18 h / -78 °C

With sodium tetrahydroborate; formic acid; tetrachlorosilane; chiral Denmark's bisphosphoramide catalyst; diethyl methoxy borane; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1002/anie.200500564