Optical Resolving Ability of 3,5-Dimethylphenylcarbamates of Oligosaccharides and Cyclodextrins

Abstract

Abstract 3,5-Dimethylphenylcarbamates of oligosaccharides and cyclodextrins were synthesized and their chiral recognition abilities were evaluated as chiral stationary phases for high-performance liquid chromatography. In case of the carbamates of linear maltooligosaccharides, the optical resolution abilities of 4–7-mer were similar to each other and were not so different from the ability of amylose tris(3,5-dimethylphenylcarbamate). The chiral recognition abilities of the carbamates of cellooligosaccharides were lower than that of the cellulose tris(3,5-dimethylphenylcarbamate). The intensities of the CD spectra of the cellooligosaccharide derivatives were smaller than that of the cellulose derivative. These results suggest that the less ordered structure of the cellooligosaccharide derivatives may be correlated to the lower chiral recognition. On the other hand, 3,5-dimethylphenylcarbamates of cydodextrins showed quite different optical resolution abilities from that of amylose tris(3,5-dimethylphenylcarbamate), probably because of a quite different high-order structure.