(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadec-5-en-1-ol

Base Information

Chemical Name:(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadec-5-en-1-ol
CAS No.:870075-19-7
Molecular Formula:C₃₈H₇₀O₆Si
Molecular Weight:651.056
Hs Code.:

(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadec-5-en-1-ol

Synonyms:(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadec-5-en-1-ol

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Chemical Property of (Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadec-5-en-1-ol

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Technology Process of (Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadec-5-en-1-ol

There total 5 articles about (Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadec-5-en-1-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: 90.0%

: 870075-18-6
1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((S)-1-methyl-pentyl)-undec-6-enyloxymethyl]-4-methoxy-benzene

: 870075-19-7
(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadec-5-en-1-ol

Guidance literature:: With hydrogenchloride;
DOI:10.1021/ol052070m

Reference yield:

: 398518-64-4
(2S,3R,4R,5S,6S,Z)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2,4,6-trimethyldeca-7,9-dien-1-ol

: 870075-19-7
(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadec-5-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / H₂ / PtO₂ / ethyl acetate / 1 h

2: 95 percent / PPh₃; imidazole; I₂ / benzene; diethyl ether / 1 h / 20 °C

3: 82 percent / Cs₂CO₃ / Pd(dppf)2

4: 90 percent / aq. HCl

With 1H-imidazole; hydrogenchloride; hydrogen; iodine; caesium carbonate; triphenylphosphine; platinum(IV) oxide; bis[1,2-bis(diphenylphosphino)ferrocene]-palladium⁽⁰⁾; In diethyl ether; ethyl acetate; benzene; 3: Suzuki coupling;
DOI:10.1021/ol052070m

Reference yield:

: 870075-17-5
(2S,3R,4R,5S,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-decan-1-ol

: 870075-19-7
(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadec-5-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / PPh₃; imidazole; I₂ / benzene; diethyl ether / 1 h / 20 °C

2: 82 percent / Cs₂CO₃ / Pd(dppf)2

3: 90 percent / aq. HCl

With 1H-imidazole; hydrogenchloride; iodine; caesium carbonate; triphenylphosphine; bis[1,2-bis(diphenylphosphino)ferrocene]-palladium⁽⁰⁾; In diethyl ether; benzene; 2: Suzuki coupling;
DOI:10.1021/ol052070m