Nonionic surfactants. Regioselective synthesis of fatty acid esters of alpha- and beta-glucopyranose

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 alpha- and beta-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. She condensing agent bis(2-oxo-3-oxazolidinyl) phosphinic chloride (BOP-CI) 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. OI sindona, giovanni/0000-0002-5623-5795; Liguori, Angelo/0000-0003-4483-2506

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 alpha- and beta-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. She condensing agent bis(2-oxo-3-oxazolidinyl) phosphinic chloride (BOP-CI) 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