Synthesis and characterization of 4,6-O-butylidene-N-(2-hydroxybenzylidene)-β-d-glucopyranosylamine: crystal structures of 4,6-O-butylidene-α-d-glucopyranose, 4,6-O-butylidene-β-d-glucopyranosylamine and 4,6-O-butylidene-N-(2-hydroxybenzylidene)-β-d-gluco

4,6-O-Butylidene-N-(2-hydroxybenzylidene)-β-d-glucopyranosylamine was synthesized and characterized using analytical, spectral and single-crystal X-ray diffraction methods. 1H and 13C NMR studies showed the presence of the β-anomer, which has also been confirmed by the crystal structure. The molecular structure of this compound showed the presence of the tridentate ONO ligation-core. Both precursors, 4,6-O-butylidene-α-d-glucopyranose and 4,6-O-butylidene-β-d-glucopyranosylamine were characterized using single crystal X-ray diffraction. The α-anomeric nature of the former and β-anomeric nature of the latter were proposed based on 1H NMR studies and were confirmed by determining the crystal structures. In addition, the crystal structure of 4,6-O-butylidene-β-d-glucopyranosylamine revealed the C-1N-glycosylation. In all the three molecules, the saccharide unit exhibits a 4C1 chair conformation. In the lattice, the molecules are connected by hydrogen-bond interactions. The conformation of 4,6-O-butylidene-N-(2-hydroxybenzylidene)-β-d-glucopyranosylamine is stabilized via an OH⋯N intramolecular interaction, and each molecule in the lattice interacts with three neighboring molecules through hydrogen bonds of the type OH⋯O and CH⋯O.