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Semipreparative-scale gas-chromatographic separation of filbertone enantiomers

✍ Scribed by Gracia Patricia Blanch; Marisa L. Ruiz del Castillo

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
756 KB
Volume
29
Category
Article
ISSN
1615-9306

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✦ Synopsis

Semipreparative-scale gas-chromatographic separation of filbertone enantiomers

The enantioselectivity of heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl-b-CD) toward racemic filbertone (E-5-methyl-hep-2-en-4-one) was studied by performing the chiral separation on a capillary column, a thick-film wide-bore column and a semipreparative column. The semipreparative enantioseparation of filbertone was achieved at 808C by using a packed column providing (R)-and (S)-enantiomers of filbertone with ee 90 and 96%, respectively. The isolated enantiomers (approximately 250 lg each, ee = 90-96%) may be used for studies on the relationship of chirality and biological activity by olfactory screening and toxicological studies.

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Table 1 Gas chromatographic data of the enantiomer separation on pern-pentylated amylose.