Analogues of uridine 5′-diphosphate glucose and guanosine 5′-diphosphate mannose

One-pot coupling of 2′,3′-di-O-benzoyl-uridine and 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-ido-octitol with appropriate bifunctional phosphoro-, phosphono- and thiophosphonylation reagents gave, after removal of the base-labile protecting groups, analogues of UDP-Glc containing charged phosphate, neutral alkyl- and arylphosphonate and phosphonothioate linkages. In an analogous manner, GDP-Man analogues, in which guanosine and octitol units are similarly linked via phosphate, alkyl phosphate or phosphotriester bonds, were prepared.