dc.contributor.author | Bhatt, Beenu | |
dc.contributor.author | Thomson, Robin J | |
dc.contributor.author | von Itzstein, Mark | |
dc.date.accessioned | 2017-05-03T15:55:45Z | |
dc.date.available | 2017-05-03T15:55:45Z | |
dc.date.issued | 2011 | |
dc.date.modified | 2012-02-16T05:34:11Z | |
dc.identifier.issn | 0022-3263 | |
dc.identifier.doi | 10.1021/jo2002193 | |
dc.identifier.uri | http://hdl.handle.net/10072/42790 | |
dc.description.abstract | Two 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.peerreviewed | Yes | |
dc.description.publicationstatus | Yes | |
dc.language | English | |
dc.publisher | American Chemical Society | |
dc.publisher.place | United States | |
dc.relation.ispartofstudentpublication | N | |
dc.relation.ispartofpagefrom | 4099 | |
dc.relation.ispartofpageto | 4104 | |
dc.relation.ispartofissue | 10 | |
dc.relation.ispartofjournal | The Journal of Organic Chemistry | |
dc.relation.ispartofvolume | 76 | |
dc.rights.retention | Y | |
dc.subject.fieldofresearch | Medicinal and biomolecular chemistry | |
dc.subject.fieldofresearch | Organic chemistry | |
dc.subject.fieldofresearch | Organic chemical synthesis | |
dc.subject.fieldofresearchcode | 3404 | |
dc.subject.fieldofresearchcode | 3405 | |
dc.subject.fieldofresearchcode | 340503 | |
dc.title | Accessing C-1 Phosphonylated 2-Acylamino Uronic Acids via 2-Nitro-glycals | |
dc.type | Journal article | |
dc.type.description | C1 - Articles | |
dc.type.code | C - Journal Articles | |
gro.faculty | Office of the Snr Dep Vice Chancellor, Institute for Glycomics | |
gro.rights.copyright | Self-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.issued | 2011 | |
gro.hasfulltext | No Full Text | |
gro.griffith.author | von Itzstein, Mark | |
gro.griffith.author | Thomson, Robin J. | |