A simple and practical approach to enantiomerically pure (S)-3-hydroxy-γ-butyrolactone: synthesis of (R)-4-cyano-3-hydroxybutyric acid ethyl ester

Kumar, Pradeep ; Deshmukh, Anis N. ; Upadhyay, Rajesh K. ; Gurjar, Mukund K. (2005) A simple and practical approach to enantiomerically pure (S)-3-hydroxy-γ-butyrolactone: synthesis of (R)-4-cyano-3-hydroxybutyric acid ethyl ester Tetrahedron: Asymmetry, 16 (16). pp. 2717-2721. ISSN 0957-4166

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S09574...

Related URL: http://dx.doi.org/10.1016/j.tetasy.2005.07.012

Abstract

The oxidation of α- or β-(1,4) linked disaccharides or oligosaccharides with cumene hydroperoxide in the presence of a base gave (S)-3,4-dihydroxybutyric acid, which was cyclized under acidic conditions to furnish (S)-3-hydroxy-γ-butyrolactone. This was subsequently converted into (R)-cyano-3-hydroxybutyric acid ethyl ester, an intermediate for statin based drugs and other related compounds.

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