SYNTHESIS OF MONOESTERS AS SURFACTANTS AND DRUGS FROM D-GLUCOSE

We have synthesized a series of monoesters from D-glucose corresponding to the structures 3-O-acyl, 6-O-acyl-1,2-O-isopropylidene-alpha-D-glucofuranose and 3-O-acyl-D-glucose, following the sequence of reactions : D-glucose -> diacetone glucose -> acylation -> partial or total deprotection. These compounds were prepared as either potential non-ionic surfactants (fatty acid esters and perfluoroalkylated ester) or antitumour drugs (n-butyric esters). Results concerning surface activity, toxicity and antitumour effects are reported. A novel method for obtaining partially deprotected 6-O-acyl esters from their corresponding 3-O-acyl isomers is reported. Deprotection conditions have been studied and a higher selectivity in partial deprotection has been achieved. We have given particular attention to the choice of solvents and reagents in order not to limit the extent to which the products might be applied.