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dc.contributor.authorBhatt, Beenu
dc.contributor.authorThomson, Robin J
dc.contributor.authorvon Itzstein, Mark
dc.date.accessioned2017-05-03T15:55:45Z
dc.date.available2017-05-03T15:55:45Z
dc.date.issued2011
dc.date.modified2012-02-16T05:34:11Z
dc.identifier.issn0022-3263
dc.identifier.doi10.1021/jo2002193
dc.identifier.urihttp://hdl.handle.net/10072/42790
dc.description.abstractTwo approaches are described for the synthesis of 2-acylamino uronic acid glycosyl phosphonates from readily accessible D-glucal. The first approach that entailed oxidation of the C-6 hydroxyl group followed by phosphonylation of the uronate 2-nitro-glycal, resulted in the formation of the ߭L-gulo-configured phosphonate. Reversing the reaction order resulted in the exclusive formation of the ߭D-gluco-configured phosphonate. In both cases the thermodynamic 1,2-trans-di-equatorial phosphonylation product is obtained.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.publisherAmerican Chemical Society
dc.publisher.placeUnited States
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom4099
dc.relation.ispartofpageto4104
dc.relation.ispartofissue10
dc.relation.ispartofjournalThe Journal of Organic Chemistry
dc.relation.ispartofvolume76
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchOrganic chemical synthesis
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode3405
dc.subject.fieldofresearchcode340503
dc.titleAccessing C-1 Phosphonylated 2-Acylamino Uronic Acids via 2-Nitro-glycals
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.facultyOffice of the Snr Dep Vice Chancellor, Institute for Glycomics
gro.rights.copyrightSelf-archiving of the author-manuscript version is not yet supported by this journal. Please refer to the journal link for access to the definitive, published version or contact the author[s] for more information.
gro.date.issued2011
gro.hasfulltextNo Full Text
gro.griffith.authorvon Itzstein, Mark
gro.griffith.authorThomson, Robin J.


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