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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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.
|Digital Object Identifier (DOI):||doi:10.1016/j.tet.2008.04.082|
|Keywords:||oxazolidines,ring-chain tautomerism, , derivatives, sugars, chiral auxiliaries, amino-acids|
Q Science > QD Chemistry
|Divisions:||University Structure - Pre August 2011 > School of Chemistry
|Date Deposited:||05 Aug 2008|
|Last Modified:||06 Aug 2015 02:43|
|RDF:||RDF+N-Triples, RDF+N3, RDF+XML, Browse.|
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