USE OF CHIRAL STATIONARY PHASES FOR THE CHROMATOGRAPHIC DETERMINATION OF ENANTIOMERIC PURITY AND ABSOLUTE-CONFIGURATION OF SOME BETA-LACTAMS

被引：36

作者：

PIRKLE, WH ^{[1
]}

TSIPOURAS, A ^{[1
]}

HYUN, MH ^{[1
]}

HART, DJ ^{[1
]}

LEE, CS ^{[1
]}

机构：

[1] OHIO STATE UNIV, DEPT CHEM, COLUMBUS, OH 43210 USA

来源：

JOURNAL OF CHROMATOGRAPHY | 1986年 / 358卷 / 02期

关键词：

D O I：

10.1016/S0021-9673(01)90351-6

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

The enantiomers of a variety of .beta.-lactams bearing aryl substituents in the 3-or 4-position have been chromatographically separated on amino acid-derived chiral stationary phases. Separation factors are typically modest. Alternatively, 3- and 4-substituted .beta.-lactams may be easily ring-opened and converted into N-3,5-dinitrobenzoyl ester derivatives of the resulting .beta.-amino acids. The enantiomers of these derivatives are readily separated on amide-derived chiral stationary phases. Aromatic substituents and not essential in the latter instances. Such separations enable accurate and convenient determination of the enantiomeric purity of the original .beta.-lactam and, in many instances, assignment of the absolute configuration of the major enantiomer of the .beta.-amino acid derivatives and hence the .beta.-lactam precursors.

引用

页码：377 / 384

页数：8

共 11 条

[1] THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .2. THE 1ST ENANTIOSELECTIVE SYNTHESIS OF THE CARBACEPHALOSPORIN NUCLEUS [J].