Accessing C-1 Phosphonylated 2-Acylamino Uronic Acids via 2-Nitro-glycals

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Title Accessing C-1 Phosphonylated 2-Acylamino Uronic Acids via 2-Nitro-glycals
Author Bhatt, Beenu; Thomson, Robin Joy; von Itzstein, Mark
Journal Name The Journal of Organic Chemistry
Year Published 2011
Place of publication United States
Publisher American Chemical Society
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 β-L-gulo-configured phosphonate. Reversing the reaction order resulted in the exclusive formation of the β-D-gluco-configured phosphonate. In both cases the thermodynamic 1,2-trans-di-equatorial phosphonylation product is obtained.
Peer Reviewed Yes
Published Yes
Alternative URI http://dx.doi.org/10.1021/jo2002193
Copyright Statement 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.
Volume 76
Issue Number 10
Page from 4099
Page to 4104
ISSN 0022-3263
Date Accessioned 2011-12-20; 2012-02-16T05:34:11Z
Research Centre Institute for Glycomics
Faculty Faculty of Science, Environment, Engineering and Technology
Subject Organic Chemical Synthesis
URI http://hdl.handle.net/10072/42790
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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