Benzoylated deoxyfluoropyranosides have been synthesized, starting with protected, unprotected, or fluorinated precursors. Fluorination of eight derivatives was compared using DAST and Deoxo-Fluor as reagents. Deoxo-Fluor was found to be especially useful in the fluorination of methyl 2,3,4-O-tribenzoyl α-D-mannopyranoside and β-D-glucopyranoside, resulting in better yields and avoiding the 1,6-methoxy migration experienced with DAST for one derivative. The two reagents gave comparable yields in the fluorination of other methyl pyranosides, confirming Deoxo-Fluor as a safer alternative to DAST. Methyl α-D-mannopyranoside underwent fluorination to yield the 4,6-difluorotalopyranoside and the corresponding cyclic sulfite. The NMR spectroscopic properties of 11 benzoyl deoxy-fluoropyranosides are reported.

Hydrolysis of six methyl O‐benzoyl‐pyranosides has been investigated using Candida rugosa lipase in dioxane/buffer mixtures. The lipase catalysed the hydrolysis of all substrates in a regiospecific manner at C‐6. The rate of reaction was dependent on pyranoside structure, reaction temperature and scale, dioxane concentration and agitation speed. Starting from their C‐6 O‐benzoyl precursors, the methyl 2,3,4‐tri‐O‐benzoyl‐pyranosides of α‐D‐galactose, β‐D‐galactose, α‐D‐glucose, and methyl 2,3‐di‐O‐benzoyl‐α‐D‐galactopyranoside could be isolated in 85–96 % yield. In hydrolysis of methyl 2,3,4,6‐tetra‐O‐benzoyl‐α‐D‐glucopyranoside and methyl 2,3,4,6‐tetra‐O‐benzoyl‐β‐D‐galactopyranoside substrate inhibition were observed, which in part could be overcome by increasing the reaction volume. Methyl 2,3,4,6‐tetra‐O‐benzoyl‐β‐D‐glucopyranoside and methyl 2,3,4,6‐tetra‐O‐benzoyl‐α‐D‐mannopyranoside were poor substrates for Candida rugosa lipase and low degree of conversion towards products were obtained under all conditions. No acyl migration was detected in any of the products.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Complete assignments of (1)H- and (13)C-NMR resonances of five methyl tetra-O-benzoyl-D-pyranosides based on (1)H, (13)C, 2D DQF-COSY, HMQC, HMBC and HSQC-TOCSY experiments have been performed.

Methods were elaborated for the synthesis of new monomers, derivatives of diallylguanidine. These monomer salts (acetate and trifluoroacetates) have the ability to polymerize in water and organic solvents in the presence of radical initiators. Radical copolymerization of diallylguanidine and diallyldimethylammonium chloride was investigated. High biocide ability of obtained copolymers was demonstrated. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 91: 439–444, 2004

A chemoenzymatic approach towards benzoylated uronic acid building blocks has been investigated starting with benzoylated hexapyranosides using regioselective C-6 enzymatic hydrolysis as the key step. Two of the building blocks were reacted with the antiepileptic drug lamotrigine. Glucuronidation of lamotrigine using methyl (2,3,4-tri-O-benzoyl-α-d-glycopyranosyl bromide)uronate proceeded to give the N2-conjugate. However, lamotrigine-N2-glucuronide was most efficiently synthesised from methyl (2,3,4-tri-O-acetyl-α-d-glucopyranosyl bromide)uronate. Employing nitromethane as solvent with CdCO3 as a base lamotrigine-N2 glucuronide was prepared in a high yield (41%). Also methyl (2,3-di-O-benzoyl-4-deoxy-4-fluoro-α-d-glucosyl bromide)uronate underwent N-glucuronidation, but the product was unstable, eliminating hydrogen fluoride to give the corresponding enoate conjugate.