[(R)-2-(2-bromophenyl)-1-(tert-butyl-dimethylsilanyloxymethyl)ethyl]carbamic acid tert-butyl ester

Base Information

Chemical Name:[(R)-2-(2-bromophenyl)-1-(tert-butyl-dimethylsilanyloxymethyl)ethyl]carbamic acid tert-butyl ester
CAS No.:1338090-99-5
Molecular Formula:C₂₀H₃₄BrNO₃Si
Molecular Weight:444.484
Hs Code.:

Synonyms:[(R)-2-(2-bromophenyl)-1-(tert-butyl-dimethylsilanyloxymethyl)ethyl]carbamic acid tert-butyl ester

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Chemical Property of [(R)-2-(2-bromophenyl)-1-(tert-butyl-dimethylsilanyloxymethyl)ethyl]carbamic acid tert-butyl ester

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Technology Process of [(R)-2-(2-bromophenyl)-1-(tert-butyl-dimethylsilanyloxymethyl)ethyl]carbamic acid tert-butyl ester

There total 3 articles about [(R)-2-(2-bromophenyl)-1-(tert-butyl-dimethylsilanyloxymethyl)ethyl]carbamic acid tert-butyl ester 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%

: 583-55-1
1-Bromo-2-iodobenzene

: 1338090-89-3
(S)-4-(tert-butyl-dimethylsilanyloxymethyl)-2,2-dioxo-1,2,3-oxathiazolidine-3-carboxylic acid tert-butyl ester

: 1338090-99-5
[(R)-2-(2-bromophenyl)-1-(tert-butyl-dimethylsilanyloxymethyl)ethyl]carbamic acid tert-butyl ester

Guidance literature:: 1-Bromo-2-iodobenzene; With TurboGrignard; In diethyl ether; at -12 ℃; for 2h; Inert atmosphere;

With copper(l) iodide; In diethyl ether; at -12 ℃; for 0.5h; Inert atmosphere;

(S)-4-(tert-butyl-dimethylsilanyloxymethyl)-2,2-dioxo-1,2,3-oxathiazolidine-3-carboxylic acid tert-butyl ester; regioselective reaction; Further stages;
DOI:10.1016/j.tetlet.2011.07.123

Reference yield:

: 152491-85-5
(R)-[1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester

: 1338090-99-5
[(R)-2-(2-bromophenyl)-1-(tert-butyl-dimethylsilanyloxymethyl)ethyl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1H-imidazole; thionyl chloride / dichloromethane / 2.5 h / -10 - 20 °C / Inert atmosphere

2.1: sodium periodate; ruthenium (IV) oxide monohydrate / dichloromethane; water / 4 h / 0 - 20 °C / Inert atmosphere

3.1: TurboGrignard / diethyl ether / 2 h / -12 °C / Inert atmosphere

3.2: 0.5 h / -12 °C / Inert atmosphere

With 1H-imidazole; sodium periodate; TurboGrignard; thionyl chloride; ruthenium (IV) oxide monohydrate; In diethyl ether; dichloromethane; water; 2.1: Sharpless oxidation;
DOI:10.1016/j.tetlet.2011.07.123

Reference yield:

: tert-butyl (4S)-4-(((tert-butyldimethylsilyl)oxy)methyl)-1,2,3-oxathiazolidine-3-carboxylate 2-oxide

: 1338090-99-5
[(R)-2-(2-bromophenyl)-1-(tert-butyl-dimethylsilanyloxymethyl)ethyl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium periodate; ruthenium (IV) oxide monohydrate / dichloromethane; water / 4 h / 0 - 20 °C / Inert atmosphere

2.1: TurboGrignard / diethyl ether / 2 h / -12 °C / Inert atmosphere

2.2: 0.5 h / -12 °C / Inert atmosphere

With sodium periodate; TurboGrignard; ruthenium (IV) oxide monohydrate; In diethyl ether; dichloromethane; water; 1.1: Sharpless oxidation;
DOI:10.1016/j.tetlet.2011.07.123