Development of Highly Efficient System for Optical Resolution

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1. In order to develop efficient chiral stationary phases for high-performance liquid chromatography to separate optical isomers, various 4-alkoxyphenylcarbamates of cellulose and amylose were prepared and their optical resolving abilities were evaluated after being adsorbed on silica gel. Optical resolving ability depended on the alkoxy group introduced at 4-position, and 4-isopropoxy-, 4-isobutoxy- and 3,5-dimethyl-4-methoxyphenylcarbamates of cellulose were found to afford efficient chiral stationary phases. Various aralkylcarbamates such as benzy1-, 1-phenylethyl-, and 1-phenylpropylcarbamates of cellulose and amylose were also used as chiral stationary phases for HPLC. Among these carbamates, 1-phenylethyl-and 1-phenylpropylcarbamates showed high optical resolving power, and particularly high adility was found on amylose tris ((S)-1-phenylethylcarbamate).2. Optical resolving abilities of benzoates and phenylcarbamates of cellulose and amylose were tested by supercritical fluid chromatography (FAC). The benzoates were found to show the comparable optical resolving ability to that in HPLC.3. Optically active polyamides bearing trans-1,2-dicarboxylic acid residue was synthesized and used as chiral stationary phase to evaluate optical resolving ability.