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
ePrint ID: 54482
Date Deposited: 05 Aug 2008
Last Modified: 27 Mar 2014 18:37
URI: http://eprints.soton.ac.uk/id/eprint/54482

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