The University of Southampton
University of Southampton Institutional Repository

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
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
0040-4020
6377-6386
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.
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), 6377-6386. (doi:10.1016/j.tet.2008.04.082).

Record type: Article

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.

Full text not available from this repository.

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: 20 Jul 2019 01:10

Export record

Altmetrics

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×