Synthesis and cahracterization of 4,6-O-butylidene-N-(2-hydroxybenzylidene)-beta-D-glucopyranosylamine:crystal structures of 4,6-O-butylidene-alpha-D-glucopyranose,4,6-O-butylidene-beta-D-glucopyranosylamine and 4,6-O-butylidene-N-(2-hydroxybenzylide

摘要

4,6-O-Butylidee-N-(2-hydroxybenzylidene)-beta-D-glucopyranosylamine was synthesized and characterized using analytical,spectral and single-crsytal X-raydiffraction methods.~1H and ~(13)C NMR studies showed the presence of the beta-anomer,which tridentate ONO ligation-core.Both rpecursors,4,6-O-butylidene-alpha-D-glucopyanose and 4,6-O-butylidene-beta-D-glucopyranosylamien were characterized using single crystal X-ray diffraction.The alpha-anomeric nature of the former and beta-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-beta-D-glucopyranosylamine revealed the C-1-N-glycosylation.In all the three molecules,the saccharide unit exhibits a ~4C_1 chair conformation.In the lattice,the molecules are connected by hydrogen-bond interactions.The conformation of 4,6-O-butylidene-N-(2-hydroxybenzylidene)-beta-D-glucopyranosylamine is stabilized via an O…N intramolecula rinteraction,and each molecule in the lattice interacts with three neigh boring moelcules through hydrogen bonds of the type O-H…N intramolecular interaction,and eachmolecule in the lattice interacts with three neighboring molecules through hydrogen bonds of the type O-H…O and C-H…O.