Synthesis of partially benzylated arabinofuranosides, NMR analysis, and application to oligosaccharide synthesis
摘要:
The preparation and NMR analysis of 2,3-di-O-benzyl arabinofuranosides have been described. In DMSO-d(6), 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 alpha- or beta-linked furanosides. (C) 2010 Elsevier Ltd. All rights reserved.