NONIONIC SURFACTANTS - REGIOSELECTIVE SYNTHESIS OF FATTY-ACID ESTERS OF ALPHA-GLUCOPYRANOSE AND BETA-GLUCOPYRANOSE

Lipophilic esters of saccharides belong to the family of nonionic surf actants widely employed in pharmaceutical and cosmetics formulations. A very simple method is presented whereby 6-O-esters of alpha- and bet a-glucose can be prepared and isolated. Good results have been obtaine d in the synthesis of 6-O-oleyl derivatives by simple acylation with a ppropriate oleyl chloride. She condensing agent bis(2-oxo-3-oxazolidin yl) phosphinic chloride (BOP-CI) allows the preparations of the same e sters with better regioselectivity but with yields strongly dependent on the aliphatic chain length of the carboxylic acids employed.