(3R,4R,5S)-3-benzoyloxy-5-[(tert-butyldimethylsilyl)oxy]-4-[(2-pivaloyloxy)ethyl]-6-(tosyloxy)hex-1-ene

Base Information

Chemical Name:(3R,4R,5S)-3-benzoyloxy-5-[(tert-butyldimethylsilyl)oxy]-4-[(2-pivaloyloxy)ethyl]-6-(tosyloxy)hex-1-ene
CAS No.:1439381-82-4
Molecular Formula:C₃₃H₄₈O₈SSi
Molecular Weight:632.891
Hs Code.:

Synonyms:(3R,4R,5S)-3-benzoyloxy-5-[(tert-butyldimethylsilyl)oxy]-4-[(2-pivaloyloxy)ethyl]-6-(tosyloxy)hex-1-ene

Suppliers and Price of (3R,4R,5S)-3-benzoyloxy-5-[(tert-butyldimethylsilyl)oxy]-4-[(2-pivaloyloxy)ethyl]-6-(tosyloxy)hex-1-ene

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4R,5S)-3-benzoyloxy-5-[(tert-butyldimethylsilyl)oxy]-4-[(2-pivaloyloxy)ethyl]-6-(tosyloxy)hex-1-ene

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (3R,4R,5S)-3-benzoyloxy-5-[(tert-butyldimethylsilyl)oxy]-4-[(2-pivaloyloxy)ethyl]-6-(tosyloxy)hex-1-ene

There total 8 articles about (3R,4R,5S)-3-benzoyloxy-5-[(tert-butyldimethylsilyl)oxy]-4-[(2-pivaloyloxy)ethyl]-6-(tosyloxy)hex-1-ene 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%

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

: 98-59-9
p-toluenesulfonyl chloride

: 1439381-82-4
(3R,4R,5S)-3-benzoyloxy-5-[(tert-butyldimethylsilyl)oxy]-4-[(2-pivaloyloxy)ethyl]-6-(tosyloxy)hex-1-ene

Guidance literature:: With pyridine; at 0 - 20 ℃; for 15.5h; Inert atmosphere;
DOI:10.1021/ml400098w

Reference yield:

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

: 1439381-82-4
(3R,4R,5S)-3-benzoyloxy-5-[(tert-butyldimethylsilyl)oxy]-4-[(2-pivaloyloxy)ethyl]-6-(tosyloxy)hex-1-ene

Guidance literature:: Multi-step reaction with 7 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

7: pyridine / 15.5 h / 0 - 20 °C / Inert atmosphere

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

: 1439381-82-4
(3R,4R,5S)-3-benzoyloxy-5-[(tert-butyldimethylsilyl)oxy]-4-[(2-pivaloyloxy)ethyl]-6-(tosyloxy)hex-1-ene

Guidance literature:: Multi-step reaction with 4 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

4: pyridine / 15.5 h / 0 - 20 °C / Inert atmosphere

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