(2S,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(1-ethoxyethyl)-3-methyl-3-vinyl cyclohexanone

Base Information

Chemical Name:(2S,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(1-ethoxyethyl)-3-methyl-3-vinyl cyclohexanone
CAS No.:136635-17-1
Molecular Formula:C₂₉H₄₀O₃Si
Molecular Weight:464.72
Hs Code.:

Synonyms:(2S,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(1-ethoxyethyl)-3-methyl-3-vinyl cyclohexanone

Suppliers and Price of (2S,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(1-ethoxyethyl)-3-methyl-3-vinyl cyclohexanone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(1-ethoxyethyl)-3-methyl-3-vinyl cyclohexanone

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Technology Process of (2S,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(1-ethoxyethyl)-3-methyl-3-vinyl cyclohexanone

There total 16 articles about (2S,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(1-ethoxyethyl)-3-methyl-3-vinyl cyclohexanone 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: 71.0%

: 105-57-7,30846-29-8
diethyl acetal

: 136611-31-9
(3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-3-methyl-1-<(trimethylsilyl)oxy>-3-vinylcyclohexene

: 136635-17-1
(2R,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(1-ethoxyethyl)-3-methyl-3-vinyl cyclohexanone

: 136635-17-1
(2S,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(1-ethoxyethyl)-3-methyl-3-vinyl cyclohexanone

Guidance literature:: With tin(IV) chloride; In dichloromethane; at -75 ℃; for 1.5h;
DOI:10.1016/S0040-4020(01)86539-X

Reference yield: 71.0%

: 105-57-7,30846-29-8
diethyl acetal

: 136611-31-9
(3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-3-methyl-1-<(trimethylsilyl)oxy>-3-vinylcyclohexene

: 136635-17-1
(2R,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(1-ethoxyethyl)-3-methyl-3-vinyl cyclohexanone

: 136635-17-1
(2S,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(1-ethoxyethyl)-3-methyl-3-vinyl cyclohexanone

Guidance literature:: With tin(IV) chloride; In dichloromethane; at -75 ℃; for 1.5h;
DOI:10.1016/S0040-4020(01)86539-X

Reference yield:

: 31883-98-4
3-methylcyclohex-3-en-1-one

: 136635-17-1
(2R,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(1-ethoxyethyl)-3-methyl-3-vinyl cyclohexanone

Guidance literature:: Multi-step reaction with 7 steps

1: Na₂CO₃, peracetic acid, NaOAc / CH₂Cl₂ / 2 h

2: triethylamine / 2.5 h

3: 93 percent / Et(iPr)2N, 4-pyrrolidinopyridine / CH₂Cl₂ / 2 h

4: aq. tris(hydroxymethyl)aminomethane hydrochloride (pH 7.5) / dimethylsulfoxide / 10 h / 20 °C / Pig liver esterase

5: 95 percent / imidazol / dimethylformamide

6: 1.) CuBr*SMe₂, 2.) TMEDA / 1.) THF, -75 deg C, 20 min., 2.) THF, -75 deg C, 180 min., -> r.t., 16 h

7: 14 percent / SnCl₄ / CH₂Cl₂ / 1.5 h / -75 °C

With 1H-imidazole; peracetic acid; copper(I) bromide dimethylsulfide complex; N,N,N,N,-tetramethylethylenediamine; sodium acetate; tris hydrochloride; tin(IV) chloride; sodium carbonate; 4-pyrrolidin-1-ylpyridine; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)86539-X