Bacillus subtilis epoxide hydrolase-catalyzed preparation of enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether and its application to expeditious synthesis of (R)-bicalutamide

被引：26

作者：

Fujino, Aya

Asano, Masayoshi

Yamaguchi, Hitomi

Shirasaka, Naoki

Sakoda, Akiko

Ikunaka, Masaya

Obata, Rika

Nishiyama, Shigeru

Sugai, Takeshi

机构：

[1] Keio Univ, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

[2] Nagase & Co, Ctr Res & Dev, Nishi Ku, Kobe, Hyogo 6512241, Japan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 06期

关键词：

epoxide hydrolase; (R)-1-benzyloxy-2-methylpropane-2,3-diol; kinetic resolution; diol; bicalutamide;

D O I：

10.1016/j.tetlet.2006.12.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Expeditious synthesis of (R)-bicalutamide (1), a synthetic antiandrogen, from enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether (4) was achieved. An engineered Bacillus subtilis epoxide hydrolase worked enantioselectively on the racemic epoxide (7) to provide the above starting material in highly enantiomerically enriched state. (c) 2006 Elsevier Ltd. All rights reserved.

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页码：979 / 983

页数：5

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