ChemInform Abstract: Novel Bicyclic Donors for the Synthesis of 2-Deoxy-β-glycosides.
✍ Scribed by R. W. FRANCK; C. H. MARZABADI
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 44 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Novel Bicyclic Donors for the Synthesis of 2-Deoxy-β-glycosides.
-Treatment of the novel heterocyclic donors (V) with a variety of alcohols in the presence of TfOH results in formation of β-glycosides with excellent stereoselectivity. Subsequent desulfurization with Raney-Ni efficiently gives 2-deoxy-β-glycosides. This method can be used successfully to the synthesis of glycosidic linkages found in aureolic acid antibiotics. -(FRANCK, R. W.;
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Stable glyco-fused 1,4-oxathiine derivatives, prepared by inverse electron-demand Diels-Alder reactions between suitable 1-glycals and 3-thioxopentane-2,4-dione, have been transformed into unusual glycosyl donors which, after ''remote activation'', react efficiently with glycosyl acceptors to [a] Ce