Stereoselective synthesis of d-glycero-d-manno-heptose-1β,7-bisphosphate (HBP) from d-mannurono-2,6-lactone

Abstract

The synthesis of D-glycero-D-manno-heptose-1β,7-bisphosphate (HBP) from D-mannose is described. This synthetic approach is notable for the elongation of the seventh carbon, employing mannurono-2,6-lactone, the substrate-controlled establishment of the C-6 configuration, and the nucleophilic introduction of phosphate at the C-1 position through the utilization of 4,6-O-benzylidene-α-triflate.