An efficient and highly diastereoselective synthesis of C-glycosylated 1,3-oxazolidines from N-methyl-D-glucamine
Martinez, R.F., Avalos, M., Babiano, R., Cintas, P., Jimenez, J.L., Light, M.E., Palacios, J.C. and Perez, E.M.S. (2008) An efficient and highly diastereoselective synthesis of C-glycosylated 1,3-oxazolidines from N-methyl-D-glucamine. Tetrahedron, 64, (27), 6377-6386. (doi:10.1016/j.tet.2008.04.082).
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Description/Abstract
A one-pot procedure for preparing chiral 1,3-oxazolidines derived from N-methyl-d-glucamine and aryl aldehydes is described. It has been carried out by using readily available reagents and operationally simple conditions allowing the preparation of the acyclic C-nucleoside analogs in high yields. The structure of these derivatives has been fully characterized by NMR correlations and single-crystal X-ray diffraction. Some reactions also provide access to the corresponding tetrahydro-1,3-oxazines by an alternative ring closure. Mechanistic considerations account for the observed steric course.
| Item Type: | Article |
|---|---|
| ISSNs: | 0040-4020 (print) |
| Related URLs: | |
| Keywords: | oxazolidines,ring-chain tautomerism, , derivatives, sugars, chiral auxiliaries, amino-acids |
| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 54482 |
| Date Deposited: | 05 Aug 2008 |
| Last Modified: | 01 Jun 2011 07:03 |
| Contributors: | Martinez, R.F. (Author) Avalos, M. (Author) Babiano, R. (Author) Cintas, P. (Author) Jimenez, J.L. (Author) Light, M.E. (Author) Palacios, J.C. (Author) Perez, E.M.S. (Author) |
| Date: | 2008 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/54482 |
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