Synthesis of 6-O-Stearoyl-1,2-O-isopropylidene-α-D-glucofuranose Derivatives

ABSTRACT

This work mainly describes the selective synthesis of 6-O-stearoylation of 1,2-O-isopropylidene-α-D-gluco-furanose and subsequent testing of this compound and its derivatives for antimicrobial activity. Bisacetone D-glucose (3) was prepared from Dglucose, which upon selective deprotection of the 5,6-O-isopropylidene group gave 3,5,6- triol (4) in good yield. Unimolecular direct stearoylation of this triol at low temperature provided the desired selective 6-O-stearoate (5) in 64% yield. To further elucidate the structure and to create novel glucofuranose derivatives of biological importance, 3,5-diO-acetate (6), 3,5-di-O-mesylate (7) and 3,5-di-O-benzoate (8) were also prepared from the stearoate (5). All of the glucofuranoses (3–8) were tested via in-vitro antibacterial and antifungal functionality tests against 10 human pathogenic bacteria and 7 fungi. These experiments revealed that some of the tested glucofuranose derivatives (5, 6 and 8) showed excellent antimicrobial functionality compared to standard antibiotics.