Synthesis of partially benzylated arabinofuranosides, NMR analysis, and application to oligosaccharide synthesis

The preparation and NMR analysis of 2,3-di-O-benzyl arabinofuranosides have been described. In DMSO-d6, the sugar adopts a conformation in which the hydroxyl groups are in an equatorial position; the equilibrium composition is determined by steric factors. In CDCl3, the sugar adopts a conformation in which the intramolecular hydrogen bonding plays an important role in determining the equilibrium composition. The use of 2,3-di-O-benzyl arabinose in the synthesis of oligoarabinofuranosides enabled the synthesis of α- or β-linked furanosides.