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.
Nonionic Surfactants. Regioselective Synthesis of Fatty Acids Esters of α- and β-Glucopiranose
DE NINO, Antonio;
1997-01-01
Abstract
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.File in questo prodotto:
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