Optical Resolution on Regioselectively Carbamoylated Cellulose and Amylose with 3,5-Dimethylphenyl and 3,5-Dichlorophenyl Isocyanates

The optical resolving ability of two types of regioselectively carbamoylated cellulose and amylose with 3,5-dimethylphenyl and 3,5-dichlorophenyl isocyanates was evaluated. One had 3,5-dimethylphenylcarbamate groups at the 2 and 3 positions and a 3,5-dichlorophenylcarbamate group at the 6 position; the other had 3,5-dichlorophenylcarbamate groups at the 2 and 3 positions and a 3,5-dimethylphenylcarbamate group at the 6 position. In cellulose derivatives, the side chains at the 2,3, and 6 positions seem to interact complicatedly with racemates. On the other hand, in the amylose derivatives, the side chains at the 2 and 3 positions may mainly influence the chiral recognition ability. The optical resolving abilities of the cellulose and amylose derivatives having irregularly either 3,5-dimethylphenyl- or 3,5-dichlorophenylcarbamate groups at the 2,3, and 6 positions were also examined.