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

The preparation of eight 2,3-unsaturated -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...

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Bibliographic Details
Published in:Heterocyclic communications 2017-06, Vol.23 (3), p.205-211
Main Authors: de Melo, Adriana Cristina N., de Oliveira, Ronaldo N., de Freitas Filho, João R., da Silva, Teresinha G., Srivastava, Rajendra M.
Format: Article
Language:English
Subjects:
2,3-unsaturated glycosides
acetyl-D-galactal
acetyl-D-glucal
Alcohols
anti-inflammatory glycosides
Catalysts
Ferrier rearrangement
Heating
Irradiation
Montmorillonite
Reaction time
tri
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Summary:The preparation of eight 2,3-unsaturated -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- -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.
ISSN:0793-0283
2191-0197
DOI:10.1515/hc-2016-0226