An efficient and highly diastereoselective synthesis of C-glycosylated 1,3-oxazolidines from N-methyl-D-glucamine
An efficient and highly diastereoselective synthesis of C-glycosylated 1,3-oxazolidines from N-methyl-D-glucamine
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.
oxazolidines, ring-chain tautomerism, derivatives, sugars, chiral auxiliaries, amino-acids
6377-6386
Martinez, R.F.
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Avalos, M.
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Babiano, R.
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Cintas, P.
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Jimenez, J.L.
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Light, M.E.
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Palacios, J.C.
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Perez, E.M.S.
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2008
Martinez, R.F.
bc0a38f1-acaf-45b4-8293-e90b7e074668
Avalos, M.
d6c0ff76-2d77-4fe6-89b5-463404a42de0
Babiano, R.
d79f2a4d-a2e3-4f73-8e58-65eee2a9f88a
Cintas, P.
d4420202-106c-4e8a-b903-5deef99e6a39
Jimenez, J.L.
b07affd8-4345-44a9-b7b0-582c0d76bcf7
Light, M.E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, J.C.
db0e8c94-0385-4349-91a1-b0b2e03f4aab
Perez, E.M.S.
f5112b4f-6597-408a-b0ab-b20ec58cdea7
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), .
(doi:10.1016/j.tet.2008.04.082).
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.
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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
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Date deposited: 05 Aug 2008
Last modified: 16 Mar 2024 03:04
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Author:
R.F. Martinez
Author:
M. Avalos
Author:
R. Babiano
Author:
P. Cintas
Author:
J.L. Jimenez
Author:
J.C. Palacios
Author:
E.M.S. Perez
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