(4Z,6E)-1-(tert-butyldimethylsilyl)oxy-3,8-di[(tert-butyldiphenylsilyl)oxy]-5-phenylthio-4,6-octadiene

Base Information

Chemical Name:(4Z,6E)-1-(tert-butyldimethylsilyl)oxy-3,8-di[(tert-butyldiphenylsilyl)oxy]-5-phenylthio-4,6-octadiene
CAS No.:301310-29-2
Molecular Formula:C₅₂H₆₈O₃SSi₃
Molecular Weight:857.433
Hs Code.:

Synonyms:(4Z,6E)-1-(tert-butyldimethylsilyl)oxy-3,8-di[(tert-butyldiphenylsilyl)oxy]-5-phenylthio-4,6-octadiene

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Chemical Property of (4Z,6E)-1-(tert-butyldimethylsilyl)oxy-3,8-di[(tert-butyldiphenylsilyl)oxy]-5-phenylthio-4,6-octadiene

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Technology Process of (4Z,6E)-1-(tert-butyldimethylsilyl)oxy-3,8-di[(tert-butyldiphenylsilyl)oxy]-5-phenylthio-4,6-octadiene

There total 4 articles about (4Z,6E)-1-(tert-butyldimethylsilyl)oxy-3,8-di[(tert-butyldiphenylsilyl)oxy]-5-phenylthio-4,6-octadiene 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: 69.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 301310-28-1
(4Z,6E)-1-(tert-butyldimethylsilyl)oxy-8-(tert-butyldiphenylsilyl)oxy-5-phenylthio-4,6-octadiene-3-ol

: 301310-29-2
(4Z,6E)-1-(tert-butyldimethylsilyl)oxy-3,8-di[(tert-butyldiphenylsilyl)oxy]-5-phenylthio-4,6-octadiene

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 15h;
DOI:10.1021/jo000689q

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 301310-29-2
(4Z,6E)-1-(tert-butyldimethylsilyl)oxy-3,8-di[(tert-butyldiphenylsilyl)oxy]-5-phenylthio-4,6-octadiene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 82 percent / imidazole / dimethylformamide / 8 h / 20 °C

2.1: 73 percent / n-BiLi / hexane; tetrahydrofuran / 0.67 h / -78 °C

3.1: Red-Al / diethyl ether; toluene / 0.67 h / 0 °C

3.2: 50 percent / diethyl ether; toluene / -78 - 20 °C

4.1: 69 percent / imidazole / dimethylformamide / 15 h / 20 °C

With 1H-imidazole; n-butyllithium; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; toluene; 1.1: Condensation / 2.1: Addition / 3.1: Reduction / 3.2: Substitution / 4.1: Condensation;
DOI:10.1021/jo000689q

Reference yield:

: 81677-37-4
(E)-tert-butyl(pent-2-en-4-yn-1-yloxy)diphenylsilane

: 301310-29-2
(4Z,6E)-1-(tert-butyldimethylsilyl)oxy-3,8-di[(tert-butyldiphenylsilyl)oxy]-5-phenylthio-4,6-octadiene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 73 percent / n-BiLi / hexane; tetrahydrofuran / 0.67 h / -78 °C

2.1: Red-Al / diethyl ether; toluene / 0.67 h / 0 °C

2.2: 50 percent / diethyl ether; toluene / -78 - 20 °C

3.1: 69 percent / imidazole / dimethylformamide / 15 h / 20 °C

With 1H-imidazole; n-butyllithium; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; toluene; 1.1: Addition / 2.1: Reduction / 2.2: Substitution / 3.1: Condensation;
DOI:10.1021/jo000689q