Conversion of D-Glucose into d-Oxybiotin

Part I. Synthesis of 2, 5-Anhydro-3-azido-3-deoxy-D-xylose Dimethyl Acetal

Abstract

2, 5-Anhydro-3-azido-3-deoxy-D-xylose dimethyl acetal (XI), the key intermediate for the stereospecific synthesis of d-oxybiotin, was prepared by methanolysis of 3-azido-3-deoxy-1, 2-O-isopropylidene-5-O-P-tolylsulfonyi-α-D-xylofuranose (VIIIa) or of 3-azido-3-deoxy-1, 2-O-cyclohexylidene-5-O-p-tolylsulfonyl-α-D-xylofuranose (VIIIb).