Synthesis of glycopyranosylidene-spiro-isoxazolines

Abstract

Researchers at the University of Debrecen's Chemical Glycobiology Research Group are investigating the reactivity of anhydro-aldose-oximes derived nitrile oxides. The goal of the thesis is to examine 1,3-dipolar cycloaddition reactions of these nitrile oxides with exo-glycals. This is to form new glycopyranosylidene-spiro-isoxazoline derivatives as potential glycomimetics. The team synthesized 3,4,5,7-Tetra-O-benzoyl-2,6-anhydro-D-glycero-D-gulo-heptose-oxime(52) from 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-cyanide(46) in two steps. They also synthesized exo-glycals in two steps. The researchers carried out optimization reactions and cycloaddition reactions of oxime 52 with exo-glucal 48 and exo-glactal 50. They successfully obtained glucopyranosylidene-spiro-isoxazoline derivatives in good yields