Application of Chemoselective Pancreatin Powder-Catalyzed Deacetylation Reaction in the Synthesis of Key Statin Side Chain Intermediate (4R,6S)-4-(tert-Butyldimethylsilyloxy)-6-(hydroxymethyl)tetrahydropyran-2-one

被引：12

作者：

Troiani, Vincent ^{[1
]}

Cluzeau, Jerome ^{[1
]}

Casar, Zdenko ^{[1
]}

机构：

[1] Lek Pharmaceut Dd, Sandoz Dev Ctr Slovenia, API Dev, Dept Organ Synth, Menges 1234, Slovenia

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2011年 / 15卷 / 03期

关键词：

COA REDUCTASE INHIBITORS; CHEMOENZYMATIC SYNTHESIS; ACETYL GROUPS; EFFICIENT; MILD; BIOCATALYSIS; REAGENT; CHEMISTRY; PRECURSOR; CLEAVAGE;

D O I：

10.1021/op100341m

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A chemoselective biocatalytic procedure for the synthesis of (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one, a key lactonized statin side chain intermediate, from its acetate precursor is described. The presented method is based on the pancreatin powder-catalyzed cleavage of the acetyl group in ((2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxotetrahydro-2H-pyran-2-yl)methyl acetate. The reaction was conducted in aqueous medium. The overall process is performed in a convenient way and economical manner suitable for industrial use.

引用

页码：622 / 630

页数：9