Nonionic Surfactants. Regioselective Synthesis of Fatty Acids Esters of α- and β-Glucopiranose

Lipophilic esters of saccharides belong to the family of nonionic surfactants widely employed in pharmaceutical and cosmetics formulations. A very simple method is presented whereby 6-O-esters of α- and β-glucose can be prepared and isolated. Good results have been obtained in the synthesis of 6-O-oleyl derivatives by simple acylation with appropriate oleyl chloride. The condensing agent bis(2-oxo-3-oxazolidinyl) phosphinic chloride (BOP-Cl) allows the preparations of the same esters with better regioselectivity but with yields strongly dependent on the aliphatic chain length of the carboxylic acids employed.