SYNTHESIS OF MONOESTERS AS SURFACTANTS AND DRUGS FROM D-GLUCOSE

We have synthesized a series of monoesters from D-glucose correspondin g to the structures 3-O-acyl, -O-acyl-1,2-O-isopropylidene-alpha-D-glu cofuranose and 3-O-acyl-D-glucose, following the sequence of reactions : D-glucose -> diacetone glucose -> acylation -> partial or total dep rotection. These compounds were prepared as either potential non-ionic surfactants (fatty acid esters and perfluoroalkylated ester) or antit umour drugs (n-butyric esters). Results concerning surface activity, t oxicity and antitumour effects are reported. A novel method for obtain ing partially deprotected 6-O-acyl esters from their corresponding 3-O -acyl isomers is reported. Deprotection conditions have been studied a nd 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 appli ed.