(E)-(S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undec-4-en-3-one

Base Information

Chemical Name:(E)-(S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undec-4-en-3-one
CAS No.:790699-65-9
Molecular Formula:C₃₅H₄₆O₃Si
Molecular Weight:542.834
Hs Code.:

Synonyms:(E)-(S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undec-4-en-3-one

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Chemical Property of (E)-(S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undec-4-en-3-one

Chemical Property:

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Technology Process of (E)-(S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undec-4-en-3-one

There total 11 articles about (E)-(S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undec-4-en-3-one 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:

: (S)-5-Benzyloxy-heptanal

: 790699-61-5
[4-(tert-butyl-diphenyl-silanyloxy)-1-methyl-2-oxo-butyl]-phosphonic acid diethyl ester

: 790699-65-9
(E)-(S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undec-4-en-3-one

Guidance literature:: [4-(tert-butyl-diphenyl-silanyloxy)-1-methyl-2-oxo-butyl]-phosphonic acid diethyl ester; With n-butyllithium; In tetrahydrofuran; dichloromethane; at -78 - 0 ℃; for 0.5h;

(S)-5-Benzyloxy-heptanal; In tetrahydrofuran; at -78 - 0 ℃; for 1h; Further stages.;
DOI:10.1016/j.tetlet.2004.08.099

Reference yield:

: 100-39-0
benzyl bromide

: 790699-65-9
(E)-(S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undec-4-en-3-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 92 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 1.5 h / 0 °C

2.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

4.1: CH₂Cl₂ / 3 h / 0 - 20 °C

5.1: 62 percent / LiCl; NaBH₄ / ethanol; tetrahydrofuran / 72 h / 20 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

7.1: n-BuLi / tetrahydrofuran; CH₂Cl₂ / 0.5 h / -78 - 0 °C

7.2: tetrahydrofuran / 1 h / -78 - 0 °C

With sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 6.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetlet.2004.08.099

Reference yield:

: 127047-71-6
3-(tert-butyldiphenylsilyloxy)propan-1-ol

: 790699-65-9
(E)-(S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undec-4-en-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂

1.2: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol

1.3: 82 percent / diethyl ether

2.1: 62 percent / BuLi / tetrahydrofuran

3.1: n-BuLi / tetrahydrofuran; CH₂Cl₂ / 0.5 h / -78 - 0 °C

3.2: tetrahydrofuran / 1 h / -78 - 0 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 3.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetlet.2004.08.099