New chalcone-3-O-glycoside derivatives: Synthesis and characterization

Seven novel carbohydrate conjugates of new chalcone-3-O-glycosides were synthesized and characterized. Starting from the substituted 3 '-hydroxyarylmethylacetophenone derivatives (chalcones) with alpha-acetobromoglucose in anhydrous acetone were synthesized 2,3,4,6-tetra-O-acetyl-3 '-O-beta-d-glucopyranosyloxychalcones. Deblocking the latter with CH3ONa in dry methanol results in substituted chalcone-3-O-glycosides (3 '-O-beta-d-glucopyranosyloxychalcones). The structures of the newly synthesized chalcone-3-O-glycosides were characterized based on(1)H nuclear magnetic resonance,C-13 nuclear magnetic resonance, mass spectroscopy, and Fourier-transform infrared spectroscopy.