(2S,3R,4S,5S)-1-benzyloxy-3-(t-butyldimethylsilyloxy)-2,4-dimethylhexan-5-ol

Base Information

Chemical Name:(2S,3R,4S,5S)-1-benzyloxy-3-(t-butyldimethylsilyloxy)-2,4-dimethylhexan-5-ol
CAS No.:261968-11-0
Molecular Formula:C₂₁H₃₈O₃Si
Molecular Weight:366.616
Hs Code.:

Synonyms:(2S,3R,4S,5S)-1-benzyloxy-3-(t-butyldimethylsilyloxy)-2,4-dimethylhexan-5-ol

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Chemical Property of (2S,3R,4S,5S)-1-benzyloxy-3-(t-butyldimethylsilyloxy)-2,4-dimethylhexan-5-ol

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Technology Process of (2S,3R,4S,5S)-1-benzyloxy-3-(t-butyldimethylsilyloxy)-2,4-dimethylhexan-5-ol

There total 9 articles about (2S,3R,4S,5S)-1-benzyloxy-3-(t-butyldimethylsilyloxy)-2,4-dimethylhexan-5-ol 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: 70.0%

: 261968-10-9
(2S,3R,4S,5S)-1-benzyloxy-3,5-bis-(t-butyldimethylsilyloxy)-2,4-dimethylhexane

: 261968-11-0
(2S,3R,4S,5S)-1-benzyloxy-3-(t-butyldimethylsilyloxy)-2,4-dimethylhexan-5-ol

Guidance literature:: With camphor-10-sulfonic acid; In methanol; dichloromethane; at 0 ℃; for 8h;
DOI:10.1002/(SICI)1521-3773(20000117)39:2<377::AID-ANIE377>3.0.CO;2-E

Reference yield:

: 116546-78-2
(S)-1-benzyloxy-2-methylpentan-3-one

: 261968-11-0
(2S,3R,4S,5S)-1-benzyloxy-3-(t-butyldimethylsilyloxy)-2,4-dimethylhexan-5-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: Et₃N / diethyl ether / 2 h / 0 °C

2.1: diethyl ether / 23 h / -78 - -20 °C

3.1: lithium borohydride / diethyl ether; tetrahydrofuran / 3 h / -78 °C

3.2: 30percent aq. H₂O₂; 10percent aq. NaOH / methanol / 0 - 20 °C

4.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

5.1: 69 percent / CSA / methanol; CH₂Cl₂ / 8 h / 0 °C

With 2,6-dimethylpyridine; lithium borohydride; camphor-10-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/ja011211m

Reference yield:

: 152192-50-2
C₂₅H₃₉BO₂

: 261968-11-0
(2S,3R,4S,5S)-1-benzyloxy-3-(t-butyldimethylsilyloxy)-2,4-dimethylhexan-5-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: diethyl ether / 23 h / -78 - -20 °C

2.1: lithium borohydride / diethyl ether; tetrahydrofuran / 3 h / -78 °C

2.2: 30percent aq. H₂O₂; 10percent aq. NaOH / methanol / 0 - 20 °C

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

4.1: 69 percent / CSA / methanol; CH₂Cl₂ / 8 h / 0 °C

With 2,6-dimethylpyridine; lithium borohydride; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/ja011211m