Please use this identifier to cite or link to this item: https://scidar.kg.ac.rs/handle/123456789/12034
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dc.rights.licenserestrictedAccess-
dc.contributor.authorStevanović, Dragana-
dc.contributor.authorPejović, Anka-
dc.contributor.authorDamljanović, Ivan-
dc.contributor.authorMinić, Aleksandra-
dc.contributor.authorBogdanovic, Goran A.-
dc.contributor.authorVukićević, Miomir-
dc.contributor.authorRadulovic, Niko-
dc.contributor.authorVukicevic R.-
dc.date.accessioned2021-04-20T19:51:00Z-
dc.date.available2021-04-20T19:51:00Z-
dc.date.issued2015-
dc.identifier.issn0008-6215-
dc.identifier.urihttps://scidar.kg.ac.rs/handle/123456789/12034-
dc.description.abstract© 2015 Elsevier Ltd. All rights reserved. In situ generated zirconium catalyst from a sacrificial zirconium anode was successfully applied to promote Ferrier rearrangement of 3,4,5-tri-O-acetyl-d-glucal and 6-deoxy-3,4-di-O-acetyl-l-glucal (3,4-di-O-acetyl-l-rhamnal) in the presence of three thiols and eleven thiophenols as nucleophiles. A simple constant current electrolysis (20 mA, 0.4 F mol<sup>-1</sup>) of an acetonitrile solution of lithium perchlorate (0.1 M) containing the corresponding glycal and S-nucleophiles, using a zirconium anode and a platinum cathode resulted in the successful synthesis of the corresponding 2,3-unsaturated peracetylated thioglycosides (with an average anomer ratio α/β=4.129 in the case of peracetylated d-glucal and 8.740 in the case of l-rhamnal). The same procedure proved to be appropriate in synthesizing dihydropyran derivatives ('C-glycosides') using allyltrimethylsilane as the nucleophile (only 'α-anomers' were obtained). All new compounds were fully characterized by spectral data, whereas single-crystal X-ray analysis was performed for two thioglycosides.-
dc.rightsinfo:eu-repo/semantics/restrictedAccess-
dc.sourceCarbohydrate Research-
dc.titleFerrier rearrangement promoted by an electrochemically generated zirconium catalyst-
dc.typearticle-
dc.identifier.doi10.1016/j.carres.2015.02.001-
dc.identifier.scopus2-s2.0-84923858552-
Appears in Collections:Faculty of Science, Kragujevac

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