Premium
Nonionic surfactants. Regioselective synthesis of fatty acid esters of α‐ and β‐glucopyranose
Author(s) -
De Luca Damiano,
De Nino Antonio,
Liguori Angelo,
Procopio Antonio,
Sindona Giovanni
Publication year - 1997
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-997-0071-7
Subject(s) - d glucopyranose , regioselectivity , lipidology , chemistry , clinical chemistry , fatty acid , organic chemistry , biochemistry , stereochemistry , catalysis
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.