Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols.

Show simple item record Rauter, AP en Piedade, F en Almeida, T en Ramalho, R en Ferreira, MJ en Resende, R en Amado, J en Pereira, H en Justino, J en Neves, A en Oliveira, Maria en Canda, T en
dc.coverage.spatial Netherlands en 2014-02-17T20:27:16Z en 2004-08-02 en
dc.identifier.citation Carbohydrate Research 339(11):1889-1897 02 Aug 2004 en
dc.identifier.issn 0008-6215 en
dc.identifier.uri en
dc.description.abstract Synthesis of 10-membered bislactones by PCC oxidation of methyl 2,6-di-O-pivaloyl-alpha-D-glucopyranoside and methyl 4,6-O-benzylidene-alpha-D-glucopyranoside is described, with emphasis on their structure elucidation using the information gained by combination of NMR spectroscopic techniques with X-ray diffraction data. In alternative, the use of PCC and PCC adsorbed on silica gel or alumina for the regioselective oxidation of vicinal diols in sugars is also reported. Both bislactones showed antifungal activity against Candida albicans, and were slightly active against the bacteria Bacillus subtilis. The bislactone presenting pivaloyl protecting groups also promoted some growth inhibition of Staphylococcus aureus. en
dc.language eng en
dc.relation.ispartofseries Carbohydrate Research en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from en
dc.rights.uri en
dc.subject Anti-Bacterial Agents en
dc.subject Antifungal Agents en
dc.subject Crystallography, X-Ray en
dc.subject Cyclization en
dc.subject Dimerization en
dc.subject Glucose en
dc.subject Glycols en
dc.subject Lactones en
dc.subject Macrocyclic Compounds en
dc.subject Microbial Sensitivity Tests en
dc.subject Models, Molecular en
dc.subject Molecular Conformation en
dc.subject Oxidation-Reduction en
dc.subject Pyridinium Compounds en
dc.subject Stereoisomerism en
dc.subject Structure-Activity Relationship en
dc.title Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols. en
dc.type Journal Article en
dc.identifier.doi 10.1016/j.carres.2004.06.002 en
pubs.issue 11 en
pubs.begin-page 1889 en
pubs.volume 339 en
dc.identifier.pmid 15261581 en
pubs.end-page 1897 en
dc.rights.accessrights en
pubs.subtype Article en
pubs.elements-id 163203 en
dc.identifier.pii S0008621504002459 en
pubs.record-created-at-source-date 2014-02-18 en
pubs.dimensions-id 15261581 en

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