(-)-(2S)-1-(4-bromothiazol-2-yl)-2-(t-butyldimethylsilyloxy)-2-phenylethanone

Base Information

Chemical Name:(-)-(2S)-1-(4-bromothiazol-2-yl)-2-(t-butyldimethylsilyloxy)-2-phenylethanone
CAS No.:898567-43-6
Molecular Formula:C₁₇H₂₂BrNO₂SSi
Molecular Weight:412.423
Hs Code.:

Synonyms:(-)-(2S)-1-(4-bromothiazol-2-yl)-2-(t-butyldimethylsilyloxy)-2-phenylethanone

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Chemical Property of (-)-(2S)-1-(4-bromothiazol-2-yl)-2-(t-butyldimethylsilyloxy)-2-phenylethanone

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Technology Process of (-)-(2S)-1-(4-bromothiazol-2-yl)-2-(t-butyldimethylsilyloxy)-2-phenylethanone

There total 1 articles about (-)-(2S)-1-(4-bromothiazol-2-yl)-2-(t-butyldimethylsilyloxy)-2-phenylethanone 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: 92.0%

: 135348-18-4
(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-acetic acid ethyl ester

: 4175-77-3
2,4-dibromo-1,3-thiazole

: 898567-43-6
(-)-(2S)-1-(4-bromothiazol-2-yl)-2-(t-butyldimethylsilyloxy)-2-phenylethanone

Guidance literature:: 2,4-dibromo-1,3-thiazole; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 2h;

(S)-(tert-butyl-dimethyl-silanyloxy)-phenyl-acetic acid ethyl ester; In diethyl ether; hexane; at -78 - 0 ℃;
DOI:10.1021/jo060462g

Reference yield:

: 898567-43-6
(-)-(2S)-1-(4-bromothiazol-2-yl)-2-(t-butyldimethylsilyloxy)-2-phenylethanone

: 1-(4-bromothiazol-2-yl)-2-(tert-butyldimethylsilyloxy)-2-phenylethanol

: 898567-44-7
(+)-(1R,2S)-1-(4-bromothiazol-2-yl)-2-(tert-butyldimethylsilyloxy)-2-phenylethanol

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1021/jo060462g

Reference yield:

: 898567-43-6
(-)-(2S)-1-(4-bromothiazol-2-yl)-2-(t-butyldimethylsilyloxy)-2-phenylethanone

: 898567-49-2
(-)-(1S,2S)-1-(4-bromothiazol-2-yl)-2-(t-butyldimethylsilyloxy)-2-phenylethylamine

Guidance literature:: Multi-step reaction with 6 steps

1.1: L-selectride / tetrahydrofuran / 1 h / -78 °C

2.1: 89 percent / triethylamine / CH₂Cl₂ / 1 h / -78 °C

3.1: 85 percent / HF*pyridine / 40 h

4.1: 76 percent / sodium azide / dimethylsulfoxide / 2 h / 65 °C

5.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 2 h

6.1: triphenylphosphine / benzene / 3 h

6.2: 99 percent / water / benzene / 16 h

With 2,6-dimethylpyridine; sodium azide; L-Selectride; pyridine hydrogenfluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; benzene; 6.1: Staudinger reduction;
DOI:10.1021/jo060462g