Evaluation of steric effects on the exocyclic conformations of 6-C-methyl-substituted 2-acetamido-2-deoxy-β-d-glucopyranosides Original Research Article

Introduction of a stereodefined methyl group at the C-6 position of N-acetylglucosamine mono- and disaccharides creates a strong and predictable orientational bias on the geminal C-6 hydroxyl in solution, as determined by 1H–1H and 13C–1H NMR coupling constants. The conformational directing effect is more pronounced in the disaccharides because of the greater steric demand imposed by the neighboring glycosidic unit.