Background: Carbohydrate fatty acid esters are found in important biological molecules
such as bile acid 1-O-acyl galacto and bacterial glycolipids. The synthesis of glycomimetics of those
biomolecules is required to study their structure-activity relationship.
Method: In this work a series of carbohydrate fatty acid esters were regioselectively prepared mainly
via protection and deprotection and tin-mediated strategies of partially benzyl-protected sugars, followed
by hydrogenolysis of the benzyl groups.
Results: We report here the regioselective synthesis of galactose palmitoyl esters along with other fatty
acyl galactose glycomimetics namely fucose and lactose fatty esters. 1-O-palmitoyl-, 1,6-di-Opalmitoyl-
D-galactose and 1-O-palmitoyl-L-fucose derivatives were prepared via a low-temperature
esterification of the partially benzyl-protected galactose and fucose derivatives, respectively, followed
by hydrogenolysis of the benzyl groups. The regioselective synthesis of 3'-O-acyl-D-lactosides of
palmitic and nitrobenzoic acids was accomplished using a dibutyltin oxide activation strategy of partially
protected lactoside derivatives.
Conclusion: The regioselective synthesis of galactose, fucose and lactose fatty acid esters as glycomimetics
of biological molecules containing the 1-O-fatty acyl-D-galactose moiety is reported in