Bromobenzoylation of Methyl α-D-Mannopyranoside: Synthesis and Spectral Characterization

Abstract

The widening importance of carbohydrate derivatives as unrivaled potential antimicrobial and therapeutic drugs has attracted attentionto the synthesis of mannopyranoside derivatives. In the present study, regioselective 3-bromobenzoylation of methyl α-D-mannopyranoside (1) was carried out using the direct method and gave the corresponding 6-O-(3-bromobenzoyl) derivative (2) in excellent yield. A number of 2,3,4-tri-O-acyl derivatives (3–10) of this 6-substitution product using a wide variety of acylating agents were also prepared in order to obtain newer derivatives of synthetic and biological importance. The chemical structures of the newly synthesized compounds were ascertained by analyzing their physicochemical, elemental, and spectroscopic data. Additionally, the X-ray powder diffraction (XRD) of these acylated products was studiedfor quantitatively identifying crystalline compounds.Therefore, due to the importance of carbohydrates, it might be useful to develop a good method for the synthesis of carbohydrate-based drugs of the current global situation for health and disease