Effect of the mobile phase on the retention behavior of optical isomers of the mandelic acid derivative methyl 2-phenyl-2-(tetrahydropyranyloxy) acetate by chiral HPLC.

Abstract:

:Conditions for separation of enantiomers of a mandelic acid derivative, methyl 2-phenyl-2-(tetrahydropyranyloxy) acetate (the analyte) were studied. Because of the presence of two chiral carbons, the analyte consists of four stereoisomers stable at ambient temperature. Chiral HPLC of the analyte resulted in four peaks, using an (S,S)-Whelk-O1 column with the mobile phase consisting of hexane and the t-butyl methyl ether (TBME). It was found that TBME dramatically changed the retention of the isomers, though it produced the best enantioseparation on (S,S)-Whelk-O1. The amount of TBME in the mobile phase influenced the degree of retention shift; 5% (v/v) TBME gave a bigger shift than 8% (v/v) and 10% (v/v). 2-Propanol did not produce the same results. The chiral separation was also tried on cellulose tris (3, 5-dimethyl phenylcarbamate) (CDMPC), but only three peaks were seen, indicating some but not full enantiomer resolution.

journal_name

Chirality

journal_title

Chirality

authors

Shen B,Xu X,Chen J,Zhang X,Xu B

doi

10.1002/chir.20304

subject

Has Abstract

pub_date

2006-09-01 00:00:00

pages

757-61

issue

9

eissn

0899-0042

issn

1520-636X

journal_volume

18

pub_type

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