(2S,3R,4R,5S)-5-benzyloxy-1-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexan-3-ol

Base Information

Chemical Name:(2S,3R,4R,5S)-5-benzyloxy-1-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexan-3-ol
CAS No.:1459205-23-2
Molecular Formula:C₃₁H₄₂O₃Si
Molecular Weight:490.758
Hs Code.:

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

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

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

There total 4 articles about (2S,3R,4R,5S)-5-benzyloxy-1-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexan-3-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: 89.0%

: 1459205-22-1
(2S,3S,4R,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexane-2,4-diol

: 100-39-0
benzyl bromide

: 1459205-23-2
(2S,3R,4R,5S)-5-benzyloxy-1-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexan-3-ol

Guidance literature:: (2S,3S,4R,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexane-2,4-diol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.333333h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; mineral oil; at 0 ℃; for 6h; Inert atmosphere;
DOI:10.1039/c3ra42127a

Reference yield:

: 95514-03-7
(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester

: 1459205-23-2
(2S,3R,4R,5S)-5-benzyloxy-1-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexan-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / 1 h / -15 °C

2.1: tetrahydrofuran; diethyl ether / 1 h / 0 °C / Inert atmosphere

3.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 2 h / 0 °C / Inert atmosphere

3.2: 23 h / -78 - -20 °C / Inert atmosphere

3.3: 3 h / -78 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere

4.2: 6 h / 0 °C / Inert atmosphere

With dicyclohexylboron chloride; isopropylmagnesium chloride; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; mineral oil;
DOI:10.1039/c3ra42127a

Reference yield:

: 185996-35-4
(S)-3-(tert-butyldiphenylsilyloxy)-N-methoxy-N,2-dimethylpropanamide

: 1459205-23-2
(2S,3R,4R,5S)-5-benzyloxy-1-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran; diethyl ether / 1 h / 0 °C / Inert atmosphere

2.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 2 h / 0 °C / Inert atmosphere

2.2: 23 h / -78 - -20 °C / Inert atmosphere

2.3: 3 h / -78 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere

3.2: 6 h / 0 °C / Inert atmosphere

With dicyclohexylboron chloride; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; mineral oil;
DOI:10.1039/c3ra42127a