Practical preparation of 2-azido-2-deoxy-β-d-mannopyranosyl carbonates and their application in the synthesis of oligosaccharides

Abstract: 1-O-Allyloxycarbonyl (or ethyloxycarbonyl)-2-azido-2-deoxy-3-O-benzyl (or allyl, or benzoyl)-4,6-O-isopropylidene-β-d-mannopyranose derivatives were prepared from the corresponding 2-hydroxy-β-d-glucopyranosyl carbonates in high yields via triflation of the 2-hydroxyl group and subsequent SN2 displacement with azide ion. An N-acetyl-mannosamine-containing trisaccharide, a fragment of the putative O10 antigen from Acinetobacter baumannii, was efficiently synthesized using these derivatives. [Copyright &y& Elsevier]