A convenient synthesis of GDP d-glycero-α-d-manno-heptopyranose

GDP d-glycero-α-d-manno-Heptopyranose has been prepared in good overall yield from 2,3,4,6,7-penta-O-acetyl-d-glycero-d-manno-heptopyranose by a short-step synthesis. Phosphitylation using the phosphoramidite procedure afforded the α-anomer in high selectivity. Subsequent oxidation and partial deprotection gave the acetylated phosphate derivative, which was subjected to the coupling reaction with GMP-morpholidate to furnish the acetylated heptose nucleoside diphosphate in good yield. De-O-acetylation and final purification afforded the target GDP d-glycero-α-d-manno-heptopyranose, which serves as the substrate of the heptosyl transferase in Aneurinibacillus thermoaerophilus DSM 10155 and occurs as an intermediate in the biosynthesis of GDP 6-deoxy-heptose in Yersinia pseudotuberculosis.