SYNTHESIS AND STRUCTURE OF BROMO GLYCOSYL IMINES READILY OBTAINED FROM PROTECTED GLYCOSYL AZIDES

Treatment of various furanosyl and pyranosyl azides in the presence of N-bromosuccinimide in excess led to the corresponding moderately stable glycosyl bromoimines in almost quantitative yields, except for the less reactive peracetylated alpha-D-glucopyranosyl azide and a benzyl-protected derivative. NMR analysis and crystal structure determination showed that the C=N double bond adopted a (Z) configuration in the products which resulted primarily from homolysis of a C-H bond attached to the anomeric carbon.