(2S,3R)-4-O-benzoyl-1-O-(4-bromobenzyl)-2-O-tert-butyldimethylsilyl-3-(3-hydroxypropyl)-1,2,4-butanetriol

Base Information

Chemical Name:(2S,3R)-4-O-benzoyl-1-O-(4-bromobenzyl)-2-O-tert-butyldimethylsilyl-3-(3-hydroxypropyl)-1,2,4-butanetriol
CAS No.:152732-86-0
Molecular Formula:C₂₇H₃₉BrO₅Si
Molecular Weight:551.593
Hs Code.:

Synonyms:(2S,3R)-4-O-benzoyl-1-O-(4-bromobenzyl)-2-O-tert-butyldimethylsilyl-3-(3-hydroxypropyl)-1,2,4-butanetriol

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Chemical Property of (2S,3R)-4-O-benzoyl-1-O-(4-bromobenzyl)-2-O-tert-butyldimethylsilyl-3-(3-hydroxypropyl)-1,2,4-butanetriol

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Technology Process of (2S,3R)-4-O-benzoyl-1-O-(4-bromobenzyl)-2-O-tert-butyldimethylsilyl-3-(3-hydroxypropyl)-1,2,4-butanetriol

There total 4 articles about (2S,3R)-4-O-benzoyl-1-O-(4-bromobenzyl)-2-O-tert-butyldimethylsilyl-3-(3-hydroxypropyl)-1,2,4-butanetriol 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:

: 132235-67-7
(2S,3R)-4-O-benzoyl-1-O-(p-bromobenzyl)-3-(2'-propenyl)-1,2,4-butanetriol

: 152732-86-0
(2S,3R)-4-O-benzoyl-1-O-(4-bromobenzyl)-2-O-tert-butyldimethylsilyl-3-(3-hydroxypropyl)-1,2,4-butanetriol

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / imidazole / dimethylformamide / 10 h / Ambient temperature

2: 1.) borane*dimethyl sulfide; 2.) sodium perborate / 1.) THF, 0 deg C, 10 min then r.t., 3 h; 2.) THF, H₂O, r.t., overnight

With 1H-imidazole; sodium perborate; dimethylsulfide borane complex; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)96269-6

Reference yield:

: 132235-65-5
(2S,3R)-1-O-(p-bromobenzyl)-3-(2'-propenyl)-1,2,4-butanetriol

: 152732-86-0
(2S,3R)-4-O-benzoyl-1-O-(4-bromobenzyl)-2-O-tert-butyldimethylsilyl-3-(3-hydroxypropyl)-1,2,4-butanetriol

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

2: 99 percent / imidazole / dimethylformamide / 10 h / Ambient temperature

3: 1.) borane*dimethyl sulfide; 2.) sodium perborate / 1.) THF, 0 deg C, 10 min then r.t., 3 h; 2.) THF, H₂O, r.t., overnight

With pyridine; 1H-imidazole; sodium perborate; dimethylsulfide borane complex; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)96269-6

Reference yield:

: 108267-97-6
(2S,3R)-4-(p-bromobenzyloxy)-2,3-epoxybutan-1-ol

: 152732-86-0
(2S,3R)-4-O-benzoyl-1-O-(4-bromobenzyl)-2-O-tert-butyldimethylsilyl-3-(3-hydroxypropyl)-1,2,4-butanetriol

Guidance literature:: Multi-step reaction with 4 steps

1: 69 percent / diethyl ether / -55 °C

2: 85 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3: 99 percent / imidazole / dimethylformamide / 10 h / Ambient temperature

4: 1.) borane*dimethyl sulfide; 2.) sodium perborate / 1.) THF, 0 deg C, 10 min then r.t., 3 h; 2.) THF, H₂O, r.t., overnight

With pyridine; 1H-imidazole; sodium perborate; dimethylsulfide borane complex; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)96269-6