Solution and solid-state structure of N-acetamido-3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosylamine

High resolution 1H NMR and 13C NMR spectroscopic and single crystal X-ray structural analyses of N-acetamido-3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosylamine (1), a minor product of azidonitration reaction of 3,4,6-tri-O-acetyl galactal, are reported. The solution phase studies of 1 reflect that the compound exists in 4C1 conformation with cis-orientation of the substituents at C-1 and C-2. The solid-state structure of 1 reveals that a molecule of water is entrapped in the solid state of 1 and this water molecule serves to mediate N-H...O and C-H...O interactions.