(2S,3R,4R)-4-benzoyloxy-2-(tert-butyldimethylsilyl)oxy-3-(2-pivaloyloxyethyl)hex-5-en-1-ol

Base Information

Chemical Name:(2S,3R,4R)-4-benzoyloxy-2-(tert-butyldimethylsilyl)oxy-3-(2-pivaloyloxyethyl)hex-5-en-1-ol
CAS No.:1439381-81-3
Molecular Formula:C₂₆H₄₂O₆Si
Molecular Weight:478.701
Hs Code.:

Synonyms:(2S,3R,4R)-4-benzoyloxy-2-(tert-butyldimethylsilyl)oxy-3-(2-pivaloyloxyethyl)hex-5-en-1-ol

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Chemical Property of (2S,3R,4R)-4-benzoyloxy-2-(tert-butyldimethylsilyl)oxy-3-(2-pivaloyloxyethyl)hex-5-en-1-ol

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Technology Process of (2S,3R,4R)-4-benzoyloxy-2-(tert-butyldimethylsilyl)oxy-3-(2-pivaloyloxyethyl)hex-5-en-1-ol

There total 7 articles about (2S,3R,4R)-4-benzoyloxy-2-(tert-butyldimethylsilyl)oxy-3-(2-pivaloyloxyethyl)hex-5-en-1-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%

: 1439381-80-2
methyl 4-O-benzoyl-6-bromo-2-O-(tert-butyldimethylsilyl)-3,6-dideoxy-3-C-(2-pivaloyloxyethyl)-α-D-altropyranoside

: 1439381-81-3
(2S,3R,4R)-4-benzoyloxy-2-(tert-butyldimethylsilyl)oxy-3-(2-pivaloyloxyethyl)hex-5-en-1-ol

Guidance literature:: With sodium cyanoborohydride; zinc; In propan-1-ol; water; at 20 ℃; for 0.666667h; Reflux;
DOI:10.1021/ml400098w

Reference yield:

: methyl 4,6-O-benzylidene-3-deoxy-3-C-ethenyl-α-D-altropyranoside

: 1439381-81-3
(2S,3R,4R)-4-benzoyloxy-2-(tert-butyldimethylsilyl)oxy-3-(2-pivaloyloxyethyl)hex-5-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

2: tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

3: sodium hydroxide; dihydrogen peroxide / 16 h / 20 °C / Inert atmosphere

4: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5: barium carbonate; N-Bromosuccinimide / tetrachloromethane / 2 h / 0 °C / Reflux

6: sodium cyanoborohydride; zinc / propan-1-ol; water / 0.67 h / 20 °C / Reflux

With pyridine; 2,6-dimethylpyridine; N-Bromosuccinimide; dihydrogen peroxide; sodium cyanoborohydride; barium carbonate; sodium hydroxide; zinc; In tetrahydrofuran; propan-1-ol; tetrachloromethane; dichloromethane; water;
DOI:10.1021/ml400098w

Reference yield:

: methyl 4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-(2-hydroxyethyl)-α-D-altropyranoside

: 1439381-81-3
(2S,3R,4R)-4-benzoyloxy-2-(tert-butyldimethylsilyl)oxy-3-(2-pivaloyloxyethyl)hex-5-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2: barium carbonate; N-Bromosuccinimide / tetrachloromethane / 2 h / 0 °C / Reflux

3: sodium cyanoborohydride; zinc / propan-1-ol; water / 0.67 h / 20 °C / Reflux

With pyridine; N-Bromosuccinimide; sodium cyanoborohydride; barium carbonate; zinc; In propan-1-ol; tetrachloromethane; dichloromethane; water;
DOI:10.1021/ml400098w