Stereoselective synthesis of 1,2:4,5-di-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-β-d-psicopyranose and its X-ray crystallographic analysis Original Research Article

In a novel procedure, when 3-O-benzoyl-3-C-(N-hydroxycarbamimidoyl)-1,2:4,5-di-O-isopropylidene-β-d-psicopyranose (1) is treated with acetic anhydride, chloroacetyl chloride, propanic anhydride and benzoyl chloride, the 3-O-benzoyl group undergoes an intramolecular replacement reaction with neighbouring group participation and transfer resulting in a more stable conjugated system by the formation of a 1,2,4-oxadiazol ring. A possible mechanism is reported. The structure has been determined by spectroscopic data and X-ray crystallographic analysis.