Synthesis of Fully O-Benzylated N-Linked Core Pentasaccharide Glycosyl Azide

Abstract

The fully O-benzylated pentasaccharide glycosyl azide representing the common core structure of N-glycans was synthesized. The β-mannosidic linkage was created by C-2 epimerization of the initially introduced β-d- gluco-unit via DMSO/Ac₂O oxidation followed by stereoselective reduction with tetrabutylammonium borohydride.

Keywords:

• Glycosyl azides
• N-glycopeptides
• Core-pentasaccharide
• ß-D-Manno- pyranoside
• Thioglycosides

ACKNOWLEDGMENT

We are grateful for the grant from the Hungarian National Science Foundation (OTKA-71753) and TÁMOP-4.2.1/B-09/1/KONV-2010-0007.