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An efficient and highly diastereoselective synthesis of C-glycosylated 1,3-oxazolidines from N-methyl-D-glucamine

Record type: Article

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.

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Citation

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), pp. 6377-6386. (doi:10.1016/j.tet.2008.04.082).

More information

Published date: 2008
Keywords: oxazolidines, ring-chain tautomerism, derivatives, sugars, chiral auxiliaries, amino-acids

Identifiers

Local EPrints ID: 54482
URI: http://eprints.soton.ac.uk/id/eprint/54482
ISSN: 0040-4020
PURE UUID: 8daac64e-ae3a-485b-8420-86cd5fa53035
ORCID for M.E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 05 Aug 2008
Last modified: 17 Jul 2017 14:35

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Contributors

Author: R.F. Martinez
Author: M. Avalos
Author: R. Babiano
Author: P. Cintas
Author: J.L. Jimenez
Author: M.E. Light ORCID iD
Author: J.C. Palacios
Author: E.M.S. Perez

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