Synthesis of anti-inflammatory 2,3-unsaturated O -glycosides using conventional and microwave heating techniques

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 anti-inflammatory 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.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Synthesis of anti-inflammatory 2,3-unsaturated O -glycosides using conventional and microwave heating techniques ; volume:23 ; number:3 ; year:2017 ; pages:205-211 ; extent:7 ; Heterocyclic communications ; 23, Heft 3 (2017), 205-211 (gesamt 7)

Contributors, Places and Time

• Creator: de Melo, Adriana Cristina N. ; de Oliveira, Ronaldo N. ; de Freitas Filho, João R. ; da Silva, Teresinha G. ; Srivastava, Rajendra M.

Further information

• DOI: 10.1515/hc-2016-0226
• URN: urn:nbn:de:101:1-2501130619302.177730058369
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:19 AM CEST