(1R,2R,3S,4S)-4-tert-butyldimethylsilyloxy-2-methyl-1-phenyl-1,3-pentanediol

Base Information

Chemical Name:(1R,2R,3S,4S)-4-tert-butyldimethylsilyloxy-2-methyl-1-phenyl-1,3-pentanediol
CAS No.:491589-44-7
Molecular Formula:C₁₈H₃₂O₃Si
Molecular Weight:324.536
Hs Code.:

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

Suppliers and Price of (1R,2R,3S,4S)-4-tert-butyldimethylsilyloxy-2-methyl-1-phenyl-1,3-pentanediol

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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 (1R,2R,3S,4S)-4-tert-butyldimethylsilyloxy-2-methyl-1-phenyl-1,3-pentanediol

Chemical Property:

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Technology Process of (1R,2R,3S,4S)-4-tert-butyldimethylsilyloxy-2-methyl-1-phenyl-1,3-pentanediol

There total 4 articles about (1R,2R,3S,4S)-4-tert-butyldimethylsilyloxy-2-methyl-1-phenyl-1,3-pentanediol 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: 87.0%

: 100-52-7
benzaldehyde

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

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

Guidance literature:: (S) 4-(tert-butyldimethylsilyloxy)-3-pentanone; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; Inert atmosphere;

benzaldehyde; In dichloromethane; at -78 ℃; Inert atmosphere;

With lithium borohydride; In tetrahydrofuran; dichloromethane; at -78 ℃; for 1h; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201000293

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

Reference yield:

: 100-52-7
benzaldehyde

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

Guidance literature:: Multi-step reaction with 2 steps

1.1: Et₃N / diethyl ether / 2 h / -78 °C

1.2: -78 - -20 °C

1.3: 90 percent / Et₃N; LiBH₄ / tetrahydrofuran / 1.5 h / -78 °C

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

With dihydrogen peroxide; sodium acetate; triethylamine; In tetrahydrofuran; diethyl ether; water;
DOI:10.1016/S0040-4039(02)01289-3