(2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enyl toluene-4-sulfonate

Base Information

Chemical Name:(2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enyl toluene-4-sulfonate
CAS No.:916452-47-6
Molecular Formula:C₂₀H₃₄O₅SSi
Molecular Weight:414.638
Hs Code.:

Synonyms:(2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enyl toluene-4-sulfonate

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Chemical Property of (2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enyl toluene-4-sulfonate

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Technology Process of (2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enyl toluene-4-sulfonate

There total 2 articles about (2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enyl toluene-4-sulfonate 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: 90.0%

: 916452-46-5
(2S,3S)-5-(tert-butyldimethylsilanyloxy)-2-vinylpentane-1,3-diol

: 98-59-9
p-toluenesulfonyl chloride

: 916452-47-6
(2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enyl toluene-4-sulfonate

Guidance literature:: With pyridine; at 20 ℃; for 5h;
DOI:10.1016/j.bmc.2006.07.019

Reference yield:

: 299204-04-9
(4R,5S)-3-{(2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enoyl}-4-methyl-5-phenyloxazolidin-2-one

: 916452-47-6
(2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enyl toluene-4-sulfonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: tributylborane; acetic acid / tetrahydrofuran / 0.5 h / 0 °C

1.2: 88 percent / lithium borohydride / tetrahydrofuran / -78 - 0 °C

2.1: 90 percent / pyridine / 5 h / 20 °C

With pyridine; tributyl borane; acetic acid; In tetrahydrofuran;
DOI:10.1016/j.bmc.2006.07.019

Reference yield:

: 916452-47-6
(2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enyl toluene-4-sulfonate

: 2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-(4-methoxymethoxymethyl-phenyl)-2-methyl-but-3-enyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 73 percent / sodium borohydride / dimethylsulfoxide / 2 h / 20 °C

2: 100 percent / 4-(dimethylamino)pyridine; 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 2 h / 20 °C

3: 79 percent / PPh₃; tetra-n-butylammonium chloride; NaHCO₃ / Pd(OAc)2 / acetonitrile / 80 °C

With dmap; sodium tetrahydroborate; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; triphenylphosphine; palladium diacetate; In dichloromethane; dimethyl sulfoxide; acetonitrile; 3: Heck reaction;
DOI:10.1016/j.bmc.2006.07.019