A simple and practical approach to enantiomerically pure (S)-3-hydroxy-γ-butyrolactone: synthesis of (R)-4-cyano-3-hydroxybutyric acid ethyl ester |
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| Affiliation: | 1. Facultad de Matemática, Astronomía, Física y Computación (FaMAF), Universidad Nacional de Córdoba, IFEG, CONICET, Medina Allende s/n, Ciudad Universitaria, Córdoba, Argentina;2. Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, INFIQC, CONICET, Haya de la Torre s/n, Ciudad Universitaria, Córdoba, Argentina;3. DiQuiMMAI, Facultad de Ingeniería, Universidad de Buenos Aires, INTECIN, CONICET, Av. Paseo Colón 850, Buenos Aires, Argentina;1. Laboratory of Growth Regulators, Palacký University & Institute of Experimental Botany AS CR, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic;2. Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-783 71 Olomouc, Czech Republic |
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| 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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