(2R,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(cyclohexyl-<(3-hydroxypropyl)oxy>methyl)-3-methyl-3-vinylcyclohexanone

Base Information

Chemical Name:(2R,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(cyclohexyl-<(3-hydroxypropyl)oxy>methyl)-3-methyl-3-vinylcyclohexanone
CAS No.:136611-33-1
Molecular Formula:C₃₅H₅₀O₄Si
Molecular Weight:562.865
Hs Code.:

Synonyms:(2R,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(cyclohexyl-<(3-hydroxypropyl)oxy>methyl)-3-methyl-3-vinylcyclohexanone

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Chemical Property of (2R,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(cyclohexyl-<(3-hydroxypropyl)oxy>methyl)-3-methyl-3-vinylcyclohexanone

Chemical Property:

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Technology Process of (2R,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(cyclohexyl-<(3-hydroxypropyl)oxy>methyl)-3-methyl-3-vinylcyclohexanone

There total 8 articles about (2R,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(cyclohexyl-<(3-hydroxypropyl)oxy>methyl)-3-methyl-3-vinylcyclohexanone 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: 60.0%

: 76241-77-5
Cyclohexanecarbaldehyde trimethylene acetal

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

: 136611-33-1
(2R,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(cyclohexyl-<(3-hydroxypropyl)oxy>methyl)-3-methyl-3-vinylcyclohexanone

Guidance literature:: With titanium tetrachloride; In dichloromethane; at -75 ℃; for 1h;
DOI:10.1016/S0040-4020(01)86539-X

Reference yield:

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

: 136611-33-1
(2R,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(cyclohexyl-<(3-hydroxypropyl)oxy>methyl)-3-methyl-3-vinylcyclohexanone

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: 60 percent / TiCl₄ / CH₂Cl₂ / 1 h / -75 °C

With 1H-imidazole; peracetic acid; copper(I) bromide dimethylsulfide complex; N,N,N,N,-tetramethylethylenediamine; sodium acetate; tris hydrochloride; titanium tetrachloride; 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

Reference yield:

: 57356-77-1
4-acetoxy-3-methyl-2-cyclohexen-1-one

: 136611-33-1
(2R,3S,4S)-4-<(t-butyldiphenylsilyl)oxy>-2-(cyclohexyl-<(3-hydroxypropyl)oxy>methyl)-3-methyl-3-vinylcyclohexanone

Guidance literature:: Multi-step reaction with 4 steps

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

2: 95 percent / imidazol / dimethylformamide

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

4: 60 percent / TiCl₄ / CH₂Cl₂ / 1 h / -75 °C

With 1H-imidazole; copper(I) bromide dimethylsulfide complex; N,N,N,N,-tetramethylethylenediamine; tris hydrochloride; titanium tetrachloride; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)86539-X