Glycosylamines of 4,6-O-butylidene-α-D-glucopyranose: synthesis and characterization of glycosylamines, and the crystal structure of 4,6-O-butylidene-N-(o-chlorophenyl)-β-D-glucopyranosylamine

Abstract

A total of nine glycosylamines of 4,6-O-butylidene-α-D-glucopyranose were synthesized using primary amines having various groups in their ortho- or para-positions. Among these, six are monoglycosylamines, including one primary glycosylamine, and three are bis-glycosylamines. All these compounds were characterized by ¹H, ¹H-¹H COSY, ¹H-¹³C COSY and ¹³C NMR spectroscopy and FTIR spectra. The FAB mass spectra provided the molecular weights of the products by exhibiting the corresponding molecular ion peaks. The crystal structure of 4,6-O-butylidene-N-(o-chlorophenyl)-β-D-glucopyranosylamine revealed the C-1 glycosylation, the β-anomeric nature, and the ⁴C₁ chair conformation of the saccharide unit in the product. In the lattice two types of dimers exist. While one type of dimer is formed through O-H···O type of interactions, the other type is formed via C-H···O type of interactions. In the direction of these C-H···O type of interactions, the dimeric units are connected to form a chain.