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

Abstract

Seven novel carbohydrate conjugates of new chalcone-3- O-glycosides were synthesized and characterized. Starting from the substituted 3′-hydroxyarylmethylacetophenone derivatives (chalcones) with α-acetobromoglucose in anhydrous acetone were synthesized 2,3,4,6-tetra- O-acetyl-3′- O-β-d-glucopyranosyloxychalcones. Deblocking the latter with CH3ONa in dry methanol results in substituted chalcone-3- O-glycosides (3′- O-β-d-glucopyranosyloxychalcones). The structures of the newly synthesized chalcone-3- O-glycosides were characterized based on1H nuclear magnetic resonance,13C nuclear magnetic resonance, mass spectroscopy, and Fourier-transform infrared spectroscopy.