INSOLUBILIZED POLYSACCHARIDE DERIVATIVES BY BRIDGING THEIR CHAINS. THEIR USE AS STATIONARY CHIRAL PHASES AND ENANTIOSELECTIVE MEMBRANES FOR THE SEPARATION OF ENANTIOMERS

摘要

Derivatives of polysaccharides insolubilized by bridging their chains. Their use as stationary chiral phases and enantioselective membranes for the separation of enantiomers. The stationary chiral phases, the selector of which is a polysaccharide derivative, are those which are most used for the resolution of racemic compounds by chromatography, both on an analytical and a preparative scale. The most used stationary phases of this type consist of a polysaccharide derivative deposited on silica. The solubility of the chiral selector in many solvents makes it difficult to resolve racemic compounds poorly soluble in solvents compatible with the stability of the stationary phase. The invention relates to obtaining stationary phases in which the polysaccharide derivative is insolubilized on the surface of the support by simple bridging reaction between its chains using for this the residual free -OH functions present in the polysaccharide derivative. The bridging reaction is carried out by deposition of the polysaccharide derivative and of a polyfunctional reagent such as an acid anhydride or a diisocyanate on a support, evaporation of the solvent and dry heating of the product obtained at around 120 ° C. for approximately 1.5 hours. Then simply wash the product with a solvent such as chloroform at reflux to obtain a stable stationary phase in all the usual solvents in chromatography. The polysaccharide derivatives made insoluble according to the invention can also be used pure in the form of microbeads or membranes for the separation of chiral compounds.