(6E,8Z,11Z)-(S)-20-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

Base Information

Chemical Name:(6E,8Z,11Z)-(S)-20-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester
CAS No.:303039-10-3
Molecular Formula:C₄₃H₆₈O₄Si₂
Molecular Weight:705.182
Hs Code.:

Synonyms:(6E,8Z,11Z)-(S)-20-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

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Chemical Property of (6E,8Z,11Z)-(S)-20-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

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Technology Process of (6E,8Z,11Z)-(S)-20-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

There total 5 articles about (6E,8Z,11Z)-(S)-20-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl 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: 75.0%

: <9-(tert-Butyldimethylsiloxy)nonyl>triphenylphosphonium bromide

: 303039-08-9
(6E,8Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-11-oxo-undeca-6,8-dienoic acid methyl ester

: 303039-10-3
(6E,8Z,11Z)-(S)-20-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 - 20 ℃;
DOI:10.1016/S0040-4039(00)01064-9

Reference yield:

: 298691-03-9
methyl 5(S)-(tert-butyldiphenylsilyl)oxy-6-oxo-hexanoate

: 303039-10-3
(6E,8Z,11Z)-(S)-20-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / benzene / 4 h / Heating

2: 97 percent / LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

3: 86 percent / PPTS / ethanol / 3.5 h / 20 °C

4: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

5: 75 percent / LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

With pyridinium p-toluenesulfonate; Dess-Martin periodane; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; benzene; 1: Wittig olefination / 2: Wittig olefination / 3: Hydrolysis / 4: Oxidation / 5: Wittig olefination;
DOI:10.1016/S0040-4039(00)01064-9

Reference yield:

: 298691-05-1
(E)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-8-oxo-oct-6-enoic acid methyl ester

: 303039-10-3
(6E,8Z,11Z)-(S)-20-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

2: 86 percent / PPTS / ethanol / 3.5 h / 20 °C

3: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4: 75 percent / LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

With pyridinium p-toluenesulfonate; Dess-Martin periodane; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; 1: Wittig olefination / 2: Hydrolysis / 3: Oxidation / 4: Wittig olefination;
DOI:10.1016/S0040-4039(00)01064-9