(2S,3R,4S)-3-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanol

Base Information

Chemical Name:(2S,3R,4S)-3-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanol
CAS No.:603993-98-2
Molecular Formula:C₂₉H₄₈O₃Si₂
Molecular Weight:500.869
Hs Code.:

Synonyms:(2S,3R,4S)-3-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanol

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Chemical Property of (2S,3R,4S)-3-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanol

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Technology Process of (2S,3R,4S)-3-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanol

There total 6 articles about (2S,3R,4S)-3-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanol 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: 75.0%

: 603994-10-1
(4R,2'R,3'S,4'S)-4-benzyl-3-(5'-tert-butyldiphenylsilyloxy-3'-tert-butyldimethylsilyloxy-2',4'-dimethylpentanoyl)-2-oxazolidinone

: 603993-98-2
(2S,3R,4S)-3-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; methanol; at 0 ℃; for 1h;
DOI:10.1016/S0957-4166(03)00372-0

Reference yield:

: 92817-88-4
(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

: 603993-98-2
(2S,3R,4S)-3-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanol

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 98 percent / CH₂Cl₂ / 2 h / -78 - -10 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

3.1: 75 percent / LiBH₄ / methanol; tetrahydrofuran / 1 h / 0 °C

With 2,6-dimethylpyridine; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0957-4166(03)00372-0

Reference yield:

: 95514-04-8
(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

: 603993-98-2
(2S,3R,4S)-3-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

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

2.2: 98 percent / CH₂Cl₂ / 2 h / -78 - -10 °C

3.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

4.1: 75 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(03)00372-0