Synthesis and Spectral Characterization of 6-O-Octanoyl-1,2-Oisopropylidene-α-D-glucofuranose Derivatives

Abstract

Site selective acylation of monosaccharides and oligosaccharides is essential for the preparationof both natural and novel synthetic carbohydrate compounds, synthetic intermediates, postglycosylationmodifications, and for the preparation of therapeutic agents, including research tools for glycobiology.Hence, site-selective octanoylation of 1,2-O-isopropylidene-α-D-glucofuranose was conducted. Under lowtemperature in anhydrous pyridine, direct unimolar octanoylation of this glucofuranose without anycatalyst exhibited selectivity at the C-6 hydroxyl group. The C-6 O-octanoylglucofuranose, thus obtained,was then used to prepare three 3,5-di-O-acyl esters in a similar direct method to get novel esters ofglucofuranose. Characterization of all the glucofuranose esters by 1D and 2D spectroscopic technique isalso discussed herein.