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. 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.
De Luca
D
D
Dipartimento di Chimica, Università della Calabria, Arcavacata di Rende (CS), Italy.
De Nino
A
A
Liguori
A
A
Procopio
A
A
Sindona
G
G
D000215:Acylation; D002264:Carboxylic Acids / Q000737:chemistry; D004952:Esters; D005227:Fatty Acids / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry; D013501:Surface-Active Agents / Q000138:chemical synthesis*
D002264:Carboxylic Acids; D004952:Esters; D005227:Fatty Acids; D005960:Glucosides; D009943:Organophosphorus Compounds; D010080:Oxazoles; D013501:Surface-Active Agents; C078142:bis(2-oxo-3-oxazolidinyl)phosphinic chloride