Synthesis of isoxazolin-5-one glucosides by a cascade reaction.
Author(s)
Becker, Tobias
Max Planck Institute for Chemical Ecology
Görls, Helmar
Institute for Inorganic and Analytical Chemistry
Pauls, Gerhard
Max Planck Institute for Chemical Ecology
Wedekind, Roland
Max Planck Institute for Chemical Ecology
Kai, Marco
Max Planck Institute for Chemical Ecology
Boland, Wilhelm
Max Planck Institute for Chemical Ecology
Date issued
December 20, 2013
In
The Journal of organic chemistry
Vol
78
No
24
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.
ISSN
1520-6904
Publication type
journal article