Synthesis of new diesters of 1,4:3,6-dianhydro-d-glucitol by esterification with fatty acid chlorides

Abstract

A new series of esters was prepared by esterification of 1,4:3,6-dianhydro-o-glucitol with long chain fatty acid chlorides. The experimental conditions prevented thermal degradation of the sugar and led to diesters with a high degree of purity. The final products were readily isolated and characterized by IR and NMR. Molecular modelling confirmed that the exo and endo configurations of the o-alkyl groups of the diesters of isosorbide were retained. This work reports a novel synthesis of diesters of natural origin which shows promise in environmentally sensitive applications, such as phytosanitory adjuvants, requiring biodegradable materials as replacements for fossil-derived products.