(1R,3S,4R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-cyclohexyl-4-hydroxy-3-(2-phenylselanyl-ethyl)-hexan-2-one

Base Information

Chemical Name:(1R,3S,4R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-cyclohexyl-4-hydroxy-3-(2-phenylselanyl-ethyl)-hexan-2-one
CAS No.:82919-08-2
Molecular Formula:C₂₆H₄₄O₃SeSi
Molecular Weight:511.679
Hs Code.:

Synonyms:(1R,3S,4R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-cyclohexyl-4-hydroxy-3-(2-phenylselanyl-ethyl)-hexan-2-one

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Chemical Property of (1R,3S,4R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-cyclohexyl-4-hydroxy-3-(2-phenylselanyl-ethyl)-hexan-2-one

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Technology Process of (1R,3S,4R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-cyclohexyl-4-hydroxy-3-(2-phenylselanyl-ethyl)-hexan-2-one

There total 4 articles about (1R,3S,4R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-cyclohexyl-4-hydroxy-3-(2-phenylselanyl-ethyl)-hexan-2-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: 97.0%

: 123-38-6
propionaldehyde

: 82919-06-0
(R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-cyclohexyl-5-phenylselanyl-pentan-2-one

: 82919-08-2
(1R,3S,4R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-cyclohexyl-4-hydroxy-3-(2-phenylselanyl-ethyl)-hexan-2-one

Guidance literature:: With dicyclopentylboron trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/ja00384a060

Reference yield:

: 53585-93-6
(R)-(-)-hexahydromandelic acid

: 82919-08-2
(1R,3S,4R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-cyclohexyl-4-hydroxy-3-(2-phenylselanyl-ethyl)-hexan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: diethyl ether / 1.) -78 deg C, 2 h, 2.) 0 deg C, 6 h

2: imidazole, DMAP / tetrahydrofuran / 12 h / 70 °C

3: 91 percent / 12-crown-4 / benzene / 18 h / 70 °C

4: 97 percent / (c-C₅H₉)2BOTf, (2-C₃H₇)2NEt / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; dmap; dicyclopentylboron trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; (1,4,7,10-tetraoxacyclododecane); In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1021/ja00384a060

Reference yield:

: 82919-05-9
(R)-2-Cyclohexyl-1-cyclopropyl-2-hydroxy-ethanone

: 82919-08-2
(1R,3S,4R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-cyclohexyl-4-hydroxy-3-(2-phenylselanyl-ethyl)-hexan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: imidazole, DMAP / tetrahydrofuran / 12 h / 70 °C

2: 91 percent / 12-crown-4 / benzene / 18 h / 70 °C

3: 97 percent / (c-C₅H₉)2BOTf, (2-C₃H₇)2NEt / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; dmap; dicyclopentylboron trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; (1,4,7,10-tetraoxacyclododecane); In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/ja00384a060