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

Autor:	Jérôme Cluzeau, Zdenko Časar, Vincent Troiani
Rok vydání:	2011
Předmět:	chemistry.chemical_compound chemistry Acetylation Methyl acetate Organic Chemistry Side chain Organic chemistry Hydroxymethyl Tetrahydropyran Physical and Theoretical Chemistry Cleavage (embryo) Pancreatin powder Catalysis
Zdroj:	Organic Process Research & Development. 15:622-630
ISSN:	1520-586X 1083-6160
DOI:	10.1021/op100341m
Popis:	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.
Databáze:	OpenAIRE
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