Novel synthesis and structure of phosphanyl sugar derivatives

Article abstract of DOI:10.1080/07328309708007330

Some phosphanyl sugar derivatives, which are analogs of sugars having a phosphorus atom in place of the ring oxygen, were synthesized from 2-and 3-phospholenes as starting materials. Catalytic cis-dihydroxylation of 2-phospholene or 3-phospholene 1-oxide derivatives with osmium(VIII) oxide in the presence of a cooxidant afforded 3-deoxy-or 1-deoxy-tetrofuranose-type phosphanyl sugar derivatives, respectively. cis-Dihydroxylation of 4-acyloxy-2-phospholene 1-oxide derivatives gave tetrofuranose type phosphanyl sugar derivatives. Some of these derivatives of phosphanyl sugars were subjected to structural analyses using ¹H NMR and X-ray crystallography.