2002•PubMedRequires access

[Synthesis of a new cyclodextrin derivative and its application as CGC chiral stationary phase in determination of enantiomeric excess].

Xueyan Shi, Hongchao Guo, Min Wang, Wen-ge Jin, Jing-mei Zhou

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Abstract

A new cyclodextrin (CD) derivative, 2,6-di-O-benzyl-3-O-valeryl-beta-CD, was synthesized and characterized by 1H NMR and IR. Using the beta-CD derivative as chiral stationary phase of capillary gas chromatography, one chiral column was prepared. On this column, the enantiomeric excesses (e.e.) of 1-(2,4-dichlorophenyl) ethanol obtained by asymmetric catalytic hydrogenation of 2,4-dichloroacetophone and trans-3-propyloxiranemethanol synthesized by Sharpless epoxidation of trans-2-hexenol were determined and the catalytic reactions were evaluated. The results are satisfactory.

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What this paper is about

A new cyclodextrin (CD) derivative, 2,6-di-O-benzyl-3-O-valeryl-beta-CD, was synthesized and characterized by 1H NMR and IR. Using the beta-CD derivative as chiral stationary phase of capillary gas chromatography, one chiral column was prepared. On this column, the enantiomeric excesses (e.e.) of 1-(2,4-dichlorophenyl) ethanol obtained by asymmetric catalytic hydrogenation of 2,4-dichloroacetophone and trans-3-propyloxiranemethanol synthesized by Sharpless epoxidation of trans-2-hexenol were determined and the catalytic reactions were evaluated. The results are satisfactory.

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Available abstract

A new cyclodextrin (CD) derivative, 2,6-di-O-benzyl-3-O-valeryl-beta-CD, was synthesized and characterized by 1H NMR and IR. Using the beta-CD derivative as chiral stationary phase of capillary gas chromatography, one chiral column was prepared. On this column, the enantiomeric excesses (e.e.) of 1-(2,4-dichlorophenyl) ethanol obtained by asymmetric catalytic hydrogenation of 2,4-dichloroacetophone and trans-3-propyloxiranemethanol synthesized by Sharpless epoxidation of trans-2-hexenol were determined and the catalytic reactions were evaluated. The results are satisfactory.

Key concepts: Enantiomer, Chemistry, Derivative (finance), Cyclodextrin, Catalysis, Chiral column chromatography, Ethanol, Proton NMR

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[Synthesis of a new cyclodextrin derivative and its application as CGC chiral stationary phase in determination of enantiomeric excess]. — Research Paper | ScholarLens