Synthesis and optical resolution property of (1 -> 6)-alpha-D-glucopyranantris (phenylcarbamate) as chiral stationary phase in HPLC

The optical resolution property of 2,3,4-Tris-O-(3,5-dimethylphenylcarbamoy l)-(1 -->6)alpha -D-glucopyranan (5) toward racemic compounds has been stud ied as the chiral stationary phase (CSP) in high-performance liquid chromat ography (HPLC). For the synthesis of (1 -->6)-alpha -D-glucopyranan (4), th e ring-opening polymerization of 1,6-anhydro-2,3,4-tri-O-allyl-beta -D-gluc opyranose (1) has been proceeded through the stereoselective ring-opening m echanism to yield the 2,3,4-tri-O-allyl-(1 -->6)-alpha -D-glucopyranan (2). For chromatographic enantioseparation of ten racemates, such as troger's b ase and benzoin, using 5 as a CSP, it was found that the chiral discriminat ion ability of 5 with the high molecular weight polymer (CSP-5a) was higher than that with the low molecular weight polymer (CSP-5b). In addition, the elution tendency of racemates using CSP-5a was essentially identical with the results of enantioseparation using dextran tris(3,5-dimethylphenylcarba mate).