(1R,2R,3R,5S)-3-(tert-butyldiphenylsilyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one

Base Information

Chemical Name:(1R,2R,3R,5S)-3-(tert-butyldiphenylsilyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one
CAS No.:139236-68-3
Molecular Formula:C₂₅H₃₀O₂Si
Molecular Weight:390.598
Hs Code.:

Synonyms:(1R,2R,3R,5S)-3-(tert-butyldiphenylsilyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one

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Chemical Property of (1R,2R,3R,5S)-3-(tert-butyldiphenylsilyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one

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Technology Process of (1R,2R,3R,5S)-3-(tert-butyldiphenylsilyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one

There total 7 articles about (1R,2R,3R,5S)-3-(tert-butyldiphenylsilyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-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: 50.0%

: 139135-92-5
(2S,5S)-1-[(4R)-4-(tert-butyldiphenylsilyloxy)-5-vinylhept-6-enoyl]-2,5-dimethylpyrrolidine

: 139236-68-3
(1R,2R,3R,5S)-3-(tert-butyldiphenylsilyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one

: (1S,2S,3R,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one

: (1R,2S,3R,5S)-3-(tert-butyldiphenylsilyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one

Guidance literature:: (2S,5S)-1-[(4R)-4-(tert-butyldiphenylsilyloxy)-5-vinylhept-6-enoyl]-2,5-dimethylpyrrolidine; With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 20 ℃; for 24h;

In tetrachloromethane; water; for 5h; Heating;
DOI:10.1016/S0040-4020(03)00920-7

Reference yield:

: 139108-45-5
(2S,5S)-1-[(4R)-4-hydroxy-5-vinylhept-6-enoyl]-2,5-dimethylpyrrolidine

: 139236-68-3
(1R,2R,3R,5S)-3-(tert-butyldiphenylsilyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 100 percent / imidazole / dimethylformamide / 72 h / 60 °C

2.1: triflic anhydride; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 24 h / 20 °C

2.2: 50 percent / CCl₄; H₂O / 5 h / Heating

With 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(03)00920-7

Reference yield:

: 109774-96-1
4-Hydroxy-1-pyrrolidin-1-yl-5-vinyl-hept-6-en-1-one

: 109775-00-0,139236-65-0,139236-66-1,139236-67-2,139236-68-3
(1S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one

Guidance literature:: Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 60 °C

2: 1.) triflic anhydride, 3.) H₂O / 1.) CH₂Cl₂, 10 h, 2.) collidine, reflux, CH₂Cl₂, 3.) CCl₄, 90 deg C

With 1H-imidazole; trifluoromethylsulfonic anhydride; water; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)85171-0