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 |
| Date Available | 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 |
Please use this identifier to cite this record: http://hdl.handle.net/10072/42790
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