(2S,3R,4S)-5-Benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-1-pentanol

Base Information

Chemical Name:(2S,3R,4S)-5-Benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-1-pentanol
CAS No.:100649-11-4
Molecular Formula:C₂₀H₃₆O₃Si
Molecular Weight:352.59
Hs Code.:

Synonyms:(2S,3R,4S)-5-Benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-1-pentanol

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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 (2S,3R,4S)-5-Benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-1-pentanol

Chemical Property:

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Technology Process of (2S,3R,4S)-5-Benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-1-pentanol

There total 9 articles about (2S,3R,4S)-5-Benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-1-pentanol 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: 96.0%

: 450408-59-0
(4R,2'R,3'S,4'S)-4-benzyl-3-(5'-benzyloxy-3'-(tert-butyldimethylsilyloxy)-2',4'-dimethylpentanoyl)-2-oxazolidinone

: 100649-11-4
(2S,3R,4S)-5-Benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-1-pentanol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; methanol; at 0 ℃; for 1h;
DOI:10.1016/S0957-4166(02)00178-7

Reference yield: 33.0%

: 100649-10-3
(4R,2R,3'S,4'S)-3-<5'-Benzyloxy-3'-(tert-butyldimethylsilyloxy)-2',4'-dimethylpentanoyl>-4-isopropyl-2-oxazolidinone

: 100649-11-4
(2S,3R,4S)-5-Benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-1-pentanol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; for 48h;
DOI:10.1002/jlac.198519851203

Reference yield:

: 63930-49-4
(R)-3-(benzyloxy)-2-methylpropan-1-ol

: 100649-11-4
(2S,3R,4S)-5-Benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-1-pentanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / DMSO; oxalyl chloride / CH₂Cl₂ / 1 h / -78 °C

2.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

2.2: 81 percent / CH₂Cl₂ / 2 h / -78 - -10 °C

3.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

4.1: 96 percent / LiBH₄ / methanol; tetrahydrofuran / 1 h / 0 °C

With 2,6-dimethylpyridine; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1.1: Swern oxidation;
DOI:10.1016/S0957-4166(02)00178-7