(4S,5R,6R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-cyclohexyl-5-methyl-6-phenyl-[1,3,2]dioxaborinane

Base Information

Chemical Name:(4S,5R,6R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-cyclohexyl-5-methyl-6-phenyl-[1,3,2]dioxaborinane
CAS No.:491589-39-0
Molecular Formula:C₂₄H₄₁BO₃Si
Molecular Weight:416.484
Hs Code.:

Synonyms:(4S,5R,6R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-cyclohexyl-5-methyl-6-phenyl-[1,3,2]dioxaborinane

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Chemical Property of (4S,5R,6R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-cyclohexyl-5-methyl-6-phenyl-[1,3,2]dioxaborinane

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Technology Process of (4S,5R,6R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-cyclohexyl-5-methyl-6-phenyl-[1,3,2]dioxaborinane

There total 1 articles about (4S,5R,6R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-cyclohexyl-5-methyl-6-phenyl-[1,3,2]dioxaborinane 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: 90.0%

: 36140-19-9
dicyclohexylboron chloride

: 100-52-7
benzaldehyde

: 187590-50-7
(S) 4-(tert-butyldimethylsilyloxy)-3-pentanone

: 491589-39-0
(4S,5R,6R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-cyclohexyl-5-methyl-6-phenyl-[1,3,2]dioxaborinane

Guidance literature:: dicyclohexylboron chloride; (S) 4-(tert-butyldimethylsilyloxy)-3-pentanone; With triethylamine; In diethyl ether; at -78 ℃; for 2h;

benzaldehyde; at -78 - -20 ℃;

With lithium borohydride; triethylamine; In tetrahydrofuran; at -78 ℃; for 1.5h;
DOI:10.1016/S0040-4039(02)01289-3

Reference yield:

: 491589-39-0
(4S,5R,6R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-cyclohexyl-5-methyl-6-phenyl-[1,3,2]dioxaborinane

: tert-Butyl-dimethyl-[(S)-1-((4S,5R,6R)-2,2,5-trimethyl-6-phenyl-[1,3]dioxan-4-yl)-ethoxy]-silane

Guidance literature:: Multi-step reaction with 2 steps

1: H₂O₂; NaOAc / tetrahydrofuran; H₂O / 2 h / 20 °C

2: PPTS / CH₂Cl₂

With dihydrogen peroxide; sodium acetate; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/S0040-4039(02)01289-3

Reference yield:

: 491589-39-0
(4S,5R,6R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-cyclohexyl-5-methyl-6-phenyl-[1,3,2]dioxaborinane

: 491589-49-2
(1R,2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-1-phenyl-pentane-1,4-diol

: 491589-44-7
(1R,2R,3S,4S)-4-tert-butyldimethylsilyloxy-2-methyl-1-phenyl-1,3-pentanediol

Guidance literature:: With dihydrogen peroxide; sodium acetate; In tetrahydrofuran; water; at 20 ℃; for 2h; Title compound not separated from byproducts;
DOI:10.1016/S0040-4039(02)01289-3