Regioselective acylation of monosaccharides are highly significant for the preparation of both natural and non-natural carbohydrate compounds and their synthetic intermediates. In this respect, an efficient simple method for site selective 6-O-hexanoylation of octyl β-D-glucopyranoside (OG) at low temperature is described. The 6-O-hexanoylglucoside, thus formed, was then treated with five acyl halides and obtained novel corresponding O-acylglupyranosides at C-2, C-3 and C-4 positions with high yields. Activity spectra prediction for substances (PASS) indicated that these glucoside esters are potential against antimicrobials especially against fungi. In vitro antibacterial test indicated them as weak to moderate inhibitor of Gram-positive organisms. ADMET prediction indicated that these OGs are overall safe to use. Density functional theory (DFT) optimized electronic energy, enthalpy (ΔH), Gibbs free energy, entropy, dipole-moment (μ), and molecular electrostatic potential (MEP) are also discussed.

Benzyl -L-rhamnopyranoside, prepared by both conventional and microwave assisted glycosidation techniques, was converted into benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside which after lauroylation followed by removal of isopropylidene group gave the benzyl 4-O-lauroyl-α-L-rhamnopyranoside in good yield. Several derivatives of benzyl 4-O-lauroyl-α-L-rhamnopyranoside were prepared and assessed in vitro for their antimicrobial activity against ten human pathogenic bacteria and seven fungi. The structure activity relationship (SAR) study revealed that incorporation of 4-O-lauroyl group in rhamnopyranoside frame work along with 2,3-di-O-acyl group increased the antifungal potentiality of the rhamnopyranosides.