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
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
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DOI：
10.1021/op100341m
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发表时间：
2011-03
影响因子：
3.4
通讯作者：
Vincent Troiani;J. Cluzeau;Zdenko Časar
中科院分区：
文献类型：
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作者：
Vincent Troiani;J. Cluzeau;Zdenko Časar
描述了一种化学选择性生物催化方法，用于从其乙酸酯前体合成（4 R，6S）-4-（叔丁基二甲基硅氧基）-6-（羟甲基）四氢-2H-吡喃-2-酮，一种关键的内酯化他汀侧链中间体。所提出的方法是基于胰酶粉末催化裂解（（2S，4 R）-4-（叔丁基二甲基甲硅烷基氧基）-6-氧代四氢-2H-吡喃-2-基）乙酸甲酯中的乙酰基。反应在水性介质中进行。整个过程以适合工业应用的方便方式和经济方式进行。
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.