(2S,3R)-1-(4-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butan-2-ol

Base Information

Chemical Name:(2S,3R)-1-(4-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butan-2-ol
CAS No.:477200-70-7
Molecular Formula:C₁₈H₃₁BrO₃Si
Molecular Weight:403.432
Hs Code.:

Synonyms:(2S,3R)-1-(4-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butan-2-ol

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Chemical Property of (2S,3R)-1-(4-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butan-2-ol

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Technology Process of (2S,3R)-1-(4-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butan-2-ol

There total 4 articles about (2S,3R)-1-(4-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butan-2-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: 89.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 477200-69-4
(2R,3S)-4-(4-bromobenzyloxy)-2-methylbutane-1,3-diol

: 477200-70-7
(2S,3R)-1-(4-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butan-2-ol

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 5h;
DOI:10.1021/jo020537q

Reference yield:

: 108212-54-0
cis-4-(4-bromobenzyloxy)-but-2-en-1-ol

: 477200-70-7
(2S,3R)-1-(4-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 72 percent / t-butyl hydroperoxide; titanium(IV) isopropoxide; L-diisopropyl tartrate / molecular sieves 4 Angstroem / CH₂Cl₂; toluene / 20 h / -35 °C

2.1: cuprous iodide / diethyl ether; tetrahydrofuran / 4 h / -40 °C

2.2: 62 percent / sodium periodate / tetrahydrofuran; H₂O / 12 h

3.1: 89 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 5 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; copper(l) iodide; L-(+)-diisopropyl tartrate; triethylamine; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: Sharpless epoxidation;
DOI:10.1021/jo020537q

Reference yield:

: 589-15-1
1-bromomethyl-4-bromobenzene

: 477200-70-7
(2S,3R)-1-(4-Bromo-benzyloxy)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butan-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 15 h / 0 - 20 °C

2.1: 72 percent / t-butyl hydroperoxide; titanium(IV) isopropoxide; L-diisopropyl tartrate / molecular sieves 4 Angstroem / CH₂Cl₂; toluene / 20 h / -35 °C

3.1: cuprous iodide / diethyl ether; tetrahydrofuran / 4 h / -40 °C

3.2: 62 percent / sodium periodate / tetrahydrofuran; H₂O / 12 h

4.1: 89 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 5 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; copper(l) iodide; L-(+)-diisopropyl tartrate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 2.1: Sharpless epoxidation;
DOI:10.1021/jo020537q