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Synthesis of Isoxazolin-5-one Glucosides by a Cascade Reaction

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posted on 20.12.2013, 00:00 by Tobias Becker, Helmar Görls, Gerhard Pauls, Roland Wedekind, Marco Kai, Stephan H. von Reuß, Wilhelm Boland
A novel synthetic route was developed for the construction of isoxazolin-5-one glucosides using a cascade reaction. An X-ray crystal structure analysis of a isoxazolin-5-one glucoside confirmed the structure and stereochemistry of the heterocycle. The properties of the α- and β-anomers of the isoxazolin-5-one glucosides were compared. The first synthesis of 2-[6′-(3″-nitropropanoyl)-β-d-glucopyranosyl]-3-isoxazolin-5-one was realized by direct enzymatic esterification without need of further protective groups.