(R)-, (S)-, and (RS)-1-phenylethylcarbamates of cellulose and amylose were synthesized and used as chiral stationary phases for high-performance liquid chromatography. The chiral recognition abilities of the 1-phenylethyl derivatives depended greatly on the chirality of 1-phenylethyl groups. Among six derivatives, amylose tris((S)-1-phenylethylcarbamate) showed high optical resolving ability for many compounds.
Cellulose tris(4-t-butylphenylcarbamate) and amylose tris(4-t-butylphenylcarbamate) were adsorbed on macroporous silica gel and used as chiral stationary phases for high-performance liquid chromatography to separate racemic compounds. The carbamates, particularly cellulose derivative, exhibited remarkable optical resolving power, and resolved racemic drugs such as chloroquine and nicardipine which were not resolved on other phenylcarbamate derivatives of cellulose and amylose.
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