(5E,7Z)-3β-[(tert-butyldimethylsilyl)oxy]-11α-(3-buten-1-yl)-9,10-secocholesta-5,7,10(19)-triene

Base Information

Chemical Name:(5E,7Z)-3β-[(tert-butyldimethylsilyl)oxy]-11α-(3-buten-1-yl)-9,10-secocholesta-5,7,10(19)-triene
CAS No.:314728-34-2
Molecular Formula:C₃₇H₆₄OSi
Molecular Weight:553
Hs Code.:

Synonyms:(5E,7Z)-3β-[(tert-butyldimethylsilyl)oxy]-11α-(3-buten-1-yl)-9,10-secocholesta-5,7,10(19)-triene

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Chemical Property of (5E,7Z)-3β-[(tert-butyldimethylsilyl)oxy]-11α-(3-buten-1-yl)-9,10-secocholesta-5,7,10(19)-triene

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Technology Process of (5E,7Z)-3β-[(tert-butyldimethylsilyl)oxy]-11α-(3-buten-1-yl)-9,10-secocholesta-5,7,10(19)-triene

There total 2 articles about (5E,7Z)-3β-[(tert-butyldimethylsilyl)oxy]-11α-(3-buten-1-yl)-9,10-secocholesta-5,7,10(19)-triene 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: 84.0%

: 100858-27-3
(S)-(Z)-{2-[5-(tert-butyldimethylsiloxy)-2-methylenecyclohexylidene]ethyl}diphenylphosphine oxide

: 314728-32-0
11α-(3-buten-1-yl)-de-A,B-cholestan-8-one

: 314728-34-2
(5E,7Z)-3β-[(tert-butyldimethylsilyl)oxy]-11α-(3-buten-1-yl)-9,10-secocholesta-5,7,10(19)-triene

Guidance literature:: With n-butyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃;
DOI:10.1021/jo001084x

Reference yield:

: 116515-92-5
de-A,B-cholestan-9⁽¹¹⁾-en-8-one

: 314728-34-2
(5E,7Z)-3β-[(tert-butyldimethylsilyl)oxy]-11α-(3-buten-1-yl)-9,10-secocholesta-5,7,10(19)-triene

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / t-BuLi; CuI/n-Bu₃P / diethyl ether / -85 - -50 °C

2: 84 percent / n-BuLi / tetrahydrofuran; diethyl ether / -78 °C

With copper(l) iodide; n-butyllithium; tributylphosphine; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; 2: Wittig-Horner reaction;
DOI:10.1021/jo001084x

Reference yield: 74.0%

: 314728-34-2
(5E,7Z)-3β-[(tert-butyldimethylsilyl)oxy]-11α-(3-buten-1-yl)-9,10-secocholesta-5,7,10(19)-triene

: (S)-3-[2-[(1R,3aS,6S,7aR)-6-But-3-enyl-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexanol

: (5E,7Z)-11α,11'4α-(3-hexene-1,6-diyl)bis-9,10-secocholesta-5,7,10(19)-trien-3β-ol

Guidance literature:: (5E,7Z)-3β-[(tert-butyldimethylsilyl)oxy]-11α-(3-buten-1-yl)-9,10-secocholesta-5,7,10(19)-triene; With Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 2h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 24h; Further stages.;
DOI:10.1021/jo001084x