1-[(3S,4R,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-6-isopropenyl-3,5-dimethyl-cyclohex-1-enyl]-ethanone

Base Information

Chemical Name:1-[(3S,4R,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-6-isopropenyl-3,5-dimethyl-cyclohex-1-enyl]-ethanone
CAS No.:812649-82-4
Molecular Formula:C₁₉H₃₄O₃Si
Molecular Weight:338.563
Hs Code.:

Synonyms:1-[(3S,4R,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-6-isopropenyl-3,5-dimethyl-cyclohex-1-enyl]-ethanone

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Chemical Property of 1-[(3S,4R,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-6-isopropenyl-3,5-dimethyl-cyclohex-1-enyl]-ethanone

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Technology Process of 1-[(3S,4R,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-6-isopropenyl-3,5-dimethyl-cyclohex-1-enyl]-ethanone

There total 5 articles about 1-[(3S,4R,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-6-isopropenyl-3,5-dimethyl-cyclohex-1-enyl]-ethanone 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:

: 13291-18-4
isopropenylmagnesium bromide

: (E)-(2S,3R)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-oct-5-ene-1,7-dione

: 812649-82-4
1-[(3S,4R,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-6-isopropenyl-3,5-dimethyl-cyclohex-1-enyl]-ethanone

: 812649-75-5
(3R,4S,5R,6S)-2-Acetyl-5-(tert-butyl-dimethyl-silanyloxy)-3-isopropenyl-4,6-dimethyl-cyclohexanone

Guidance literature:: isopropenylmagnesium bromide; With copper(l) iodide; In tetrahydrofuran; at -78 - -20 ℃;

(E)-(2S,3R)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-oct-5-ene-1,7-dione; In tetrahydrofuran; at -78 - 20 ℃; Further stages. Title compound not separated from byproducts.;
DOI:10.1016/j.tetlet.2004.09.150

Reference yield:

: 812649-72-2
(2R,3R,4S)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-5-oxo-pentanal

: 812649-82-4
1-[(3S,4R,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-6-isopropenyl-3,5-dimethyl-cyclohex-1-enyl]-ethanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: 83 percent / toluene / 96 h / 80 °C

2.1: CuI / tetrahydrofuran / -78 - -20 °C

2.2: tetrahydrofuran / -78 - 20 °C

With copper(l) iodide; In tetrahydrofuran; toluene;
DOI:10.1016/j.tetlet.2004.09.150

Reference yield:

: 812649-70-0
(S)-4-Benzyl-3-[(2S,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

: 812649-82-4
1-[(3S,4R,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-6-isopropenyl-3,5-dimethyl-cyclohex-1-enyl]-ethanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: DMSO; C₂O₂Cl₂ / CH₂Cl₂ / 1.25 h / -78 °C

1.2: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

2.1: 83 percent / toluene / 96 h / 80 °C

3.1: CuI / tetrahydrofuran / -78 - -20 °C

3.2: tetrahydrofuran / -78 - 20 °C

With copper(l) iodide; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene; 1.1: Swern oxidation;
DOI:10.1016/j.tetlet.2004.09.150