Immobilization and Chiral Recognition of 3,5-Dimethylphenylcarbamates of Cellulose and Amylose Bearing 4-(Trimethoxysilyl)phenylcarbamate Groups

A small amount of 4-(trimethoxysilyl)phenyl groups was randomly introduced onto the 3,5-dimethylphenylcarbamates of cellulose and amylose by a one-pot method. The obtained derivatives were then effectively immobilized onto silica gel as chiral packing materials (CPMs) for high-performance liquid chromatography through intermolecular polycondensation of the trimethoxysilyl groups. The effects of the amount of 4-(trimethoxysilyl)phenyl groups on immobilization and enantioseparation were investigated. Also, the solvent durability of the immobilized-type CPMs was examined with the eluents containing chloroform and tetrahydrofuran. When these eluents were used, the chiral recognition abilities of the CPMs for most of the tested race-mates were improved to some extent depending on the compounds. Chirality 22:165-172, 2010. (C) 2009 Wiley-Liss, Inc.