(2Z,4R)-5-(tert-butyldiphenylsiloxy)-2,4-dimethyl-2-pentenyl bromide

Base Information

Chemical Name:(2Z,4R)-5-(tert-butyldiphenylsiloxy)-2,4-dimethyl-2-pentenyl bromide
CAS No.:322428-35-3
Molecular Formula:C₂₃H₃₁BrOSi
Molecular Weight:431.488
Hs Code.:

Synonyms:(2Z,4R)-5-(tert-butyldiphenylsiloxy)-2,4-dimethyl-2-pentenyl bromide

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Chemical Property of (2Z,4R)-5-(tert-butyldiphenylsiloxy)-2,4-dimethyl-2-pentenyl bromide

Chemical Property:

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Technology Process of (2Z,4R)-5-(tert-butyldiphenylsiloxy)-2,4-dimethyl-2-pentenyl bromide

There total 5 articles about (2Z,4R)-5-(tert-butyldiphenylsiloxy)-2,4-dimethyl-2-pentenyl bromide 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: 99.0%

: 322428-66-0
(Z,R)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpent-2-en-1-ol

: 322428-35-3
(2Z,4R)-5-(tert-butyldiphenylsiloxy)-2,4-dimethyl-2-pentenyl bromide

Guidance literature:: With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 0 - 20 ℃; for 0.333333h;
DOI:10.1016/S0040-4020(01)00593-2

Reference yield:

: 92817-88-4
(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

: 322428-35-3
(2Z,4R)-5-(tert-butyldiphenylsiloxy)-2,4-dimethyl-2-pentenyl bromide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.25 h / -78 °C

1.2: 1.13 g / tetrahydrofuran; toluene / 3 h / -78 - -10 °C

2.1: 94 percent / DIBAL / diethyl ether; hexane / 0.5 h / -78 °C

3.1: 99 percent / CBr₄; PPh₃ / acetonitrile / 0.33 h / 0 - 20 °C

With 18-crown-6 ether; carbon tetrabromide; potassium hexamethylsilazane; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; toluene; acetonitrile; 1.2: Still-Horner olefination;
DOI:10.1016/S0040-4020(01)00593-2

Reference yield:

: 95514-03-7
(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester

: 322428-35-3
(2Z,4R)-5-(tert-butyldiphenylsiloxy)-2,4-dimethyl-2-pentenyl bromide

Guidance literature:: Multi-step reaction with 4 steps

1.1: DIBAL / diethyl ether; hexane / 0.33 h / -78 °C

2.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.25 h / -78 °C

2.2: 1.13 g / tetrahydrofuran; toluene / 3 h / -78 - -10 °C

3.1: 94 percent / DIBAL / diethyl ether; hexane / 0.5 h / -78 °C

4.1: 99 percent / CBr₄; PPh₃ / acetonitrile / 0.33 h / 0 - 20 °C

With 18-crown-6 ether; carbon tetrabromide; potassium hexamethylsilazane; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; toluene; acetonitrile; 2.2: Still-Horner olefination;
DOI:10.1016/S0040-4020(01)00593-2