(2R,3S,4R)-4-(tert-Butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxy)-3-hydroxyhex-5-enyl benzoate

Base Information

Chemical Name:(2R,3S,4R)-4-(tert-Butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxy)-3-hydroxyhex-5-enyl benzoate
CAS No.:1307864-68-1
Molecular Formula:C₃₅H₄₈O₅Si₂
Molecular Weight:604.934
Hs Code.:

Synonyms:(2R,3S,4R)-4-(tert-Butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxy)-3-hydroxyhex-5-enyl benzoate

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Chemical Property of (2R,3S,4R)-4-(tert-Butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxy)-3-hydroxyhex-5-enyl benzoate

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Technology Process of (2R,3S,4R)-4-(tert-Butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxy)-3-hydroxyhex-5-enyl benzoate

There total 4 articles about (2R,3S,4R)-4-(tert-Butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxy)-3-hydroxyhex-5-enyl benzoate 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: 85.0%

: 1307864-67-0
(2R,3S,4R)-2-(tert-butyldiphenylsilyloxy)-3,4-dihydroxyhex-5-enyl benzoate

: 69739-34-0
t-butyldimethylsiyl triflate

: 1307864-68-1
(2R,3S,4R)-4-(tert-Butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxy)-3-hydroxyhex-5-enyl benzoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; regioselective reaction;
DOI:10.1016/j.tetlet.2011.01.124

Reference yield:

: 1307864-65-8
C₃₅H₄₄O₇Si

: 1307864-68-1
(2R,3S,4R)-4-(tert-Butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxy)-3-hydroxyhex-5-enyl benzoate

Guidance literature:: Multi-step reaction with 4 steps

1: copper(II) chloride dihydrate / acetonitrile / 0.75 h / 0 °C

2: 1H-imidazole; iodine; triphenylphosphine / toluene / 4 h / 110 °C

3: methanol; pyridinium p-toluenesulfonate / 20 °C

4: 2,6-dimethylpyridine / dichloromethane / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; methanol; copper(II) chloride dihydrate; iodine; pyridinium p-toluenesulfonate; triphenylphosphine; In dichloromethane; toluene; acetonitrile;
DOI:10.1016/j.tetlet.2011.01.124

Reference yield:

: 1307864-66-9
C₃₂H₄₀O₇Si

: 1307864-68-1
(2R,3S,4R)-4-(tert-Butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxy)-3-hydroxyhex-5-enyl benzoate

Guidance literature:: Multi-step reaction with 3 steps

1: 1H-imidazole; iodine; triphenylphosphine / toluene / 4 h / 110 °C

2: methanol; pyridinium p-toluenesulfonate / 20 °C

3: 2,6-dimethylpyridine / dichloromethane / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; methanol; iodine; pyridinium p-toluenesulfonate; triphenylphosphine; In dichloromethane; toluene;
DOI:10.1016/j.tetlet.2011.01.124