학술논문
Synthesis of anti-inflammatory 2,3-unsaturated O-glycosides using conventional and microwave heating techniques.
Document Type
Article
Author
Source
Subject
*ANTI-inflammatory agents
*GLYCOSIDE synthesis
*UNSATURATED compounds
*MICROWAVE heating
*ALCOHOLS (Chemical class)
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Language
ISSN
0793-0283
Abstract
The preparation of eight 2,3-unsaturated O-glycosides from D-glycals and alcohols, using montmorillonite K-10 as an acid catalyst, is described. The Ferrier rearrangement products were obtained in good yields using conventional heating and microwave irradiation but the reaction time was substantially reduced employing the latter procedure. The yields were slightly lower under microwave exposure. Five of the di-O-acetylated products were deacetylated to the glycosides in excellent yields. The acetylated products possess good antiinflammatory property suggesting that the acetyl group plays an important role in reducing the inflammation. Among the compounds tested, glycosides containing thiophene as an aglycone present much better inflammation reducing characteristics than the analogues without this function. [ABSTRACT FROM AUTHOR]