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.

In our present investigation a new series of nucleoside derivatives (2-13) were synthesized from uridine (1) via only two step reactions by direct acylation method. Firstly, uridine (1) was treated with 4-t-butylbenzoyl chloride in pyridine at -5?C and afforded the 5´-O-(4-t-butylbenzoyl)uridine derivative (2) in an excellent yield. In order to obtain newer products, the 5´-O-uridine derivative was further transformed to a series of 2´,3´-di-O-acyl derivatives (2-13) containing a wide variety of functionalities in a single molecular framework. The yields of the compounds were more than 80%. The synthesized titled compounds were characterized by their physical properties, FTIR (Fourier transform infrared spectroscopy), 1H-NMR (Nuclear magnetic resonance) spectroscopy and elemental analysis.