A novel glycosylation of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) via in situ pyranose-furanose rearrangement

Article abstract of DOI:10.1248/cpb.45.795

In studies on the glycosylation of 3-deoxy-D-glycero-D-galacto-2- nonulosonic acid (KDN) derivatives, O-glycosides of furanose-type KDN were synthesized from benzyl 4,5,7,8,9-penta-O-acetyl-2-bromo-2,3-dideoxy-D- glycero-D-galacto-2-nonulopyranosonate under Koenigs-Knorr reaction conditions. The furanoid structures of the KDN moiety were supported by with ¹H-NMR experiments, and the reaction was considered as a novel glycosylation with ring contraction, which proceeded via in situ pyranose-furanose rearrangement of the KDN moiety, and subsequent coupling with acceptors.