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

Base Information

Chemical Name:(4Z,6E)-1-(tert-butyldimethylsilyl)oxy-8-(tert-butyldiphenylsilyl)oxy-5-phenylthio-4,6-octadiene-3-ol
CAS No.:301310-28-1
Molecular Formula:C₃₆H₅₀O₃SSi₂
Molecular Weight:619.028
Hs Code.:

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

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

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

There total 4 articles about (4Z,6E)-1-(tert-butyldimethylsilyl)oxy-8-(tert-butyldiphenylsilyl)oxy-5-phenylthio-4,6-octadiene-3-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: 50.0%

: 931-59-9
benzenesulfenyl chloride

: 301310-27-0
(E)-5-(tert-butyldiphenylsilyl)oxy-3-hydroxy-8-(tert-butyldiphenylsilyl)oxyoct-6-en-4-yne

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

Guidance literature:: (E)-5-(tert-butyldiphenylsilyl)oxy-3-hydroxy-8-(tert-butyldiphenylsilyl)oxyoct-6-en-4-yne; With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene; at 0 ℃; for 0.666667h;

benzenesulfenyl chloride; In diethyl ether; toluene; at -78 - 20 ℃; Further stages.;
DOI:10.1021/jo000689q

Reference yield:

: 35042-52-5
(E)-2-penten-4-yn-1-ol

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

Guidance literature:: Multi-step reaction with 3 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

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;
DOI:10.1021/jo000689q

Reference yield:

: 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

Guidance literature:: Multi-step reaction with 3 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

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;
DOI:10.1021/jo000689q