title: Synthesis of isoxazolin-5-one glucosides by a cascade reaction.
abstract: 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.
authors.affiliation: Max Planck Institute for Chemical Ecology , Beutenberg Campus, Hans-Knoell-Straße 8, D-07745 Jena, Germany.
authors.forename: Tobias
authors.initials: T
authors.lastname: Becker
authors.forename: Helmar
authors.initials: H
authors.lastname: Görls
authors.forename: Gerhard
authors.initials: G
authors.lastname: Pauls
authors.forename: Roland
authors.initials: R
authors.lastname: Wedekind
authors.forename: Marco
authors.initials: M
authors.lastname: Kai
authors.forename: Stephan H
authors.initials: SH
authors.lastname: von Reuß
authors.forename: Wilhelm
authors.initials: W
authors.lastname: Boland
mesh_terms: D018360:Crystallography, X-Ray; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D005960:Glucosides; D007555:Isoxazoles; C013076:isoxazolin-5-one