Issue 23, 2003
From the journal:

Organic & Biomolecular Chemistry

A novel strategy towards the synthesis of orthogonally functionalised 4-aminoglycosides

Leendert J. van den Bos,a   Jeroen D.C. Codée,a   Jacques H. van Boom,a   Herman S. Overkleefta  and  Gijsbert A. van der Marel*a  

* Corresponding authors

a Leiden Institute of Chemistry, Leiden University, Gorlaeus Laboratories, PO Box 9502, 2300 RA Leiden, The Netherlands
E-mail: marel_g@chem.leidenuniv.nl
Fax: +31 71 5274307
Tel: +31 71 5274280

Abstract

A tethered nucleophilic substitution strategy for the stereoselective introduction of axially oriented amino functions on suitably protected gluco- and mannopyranosides is presented. The obtained oxazine is a versatile building block, which after some manipulation, could be used in the construction of highly functionalised oligosaccharides.

Graphical abstract: A novel strategy towards the synthesis of orthogonally functionalised 4-aminoglycosides

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Article information

DOI
https://doi.org/10.1039/B309823K
Article type
Paper
Submitted
18 Aug 2003
Accepted
26 Sep 2003
First published
21 Oct 2003

Org. Biomol. Chem., 2003,1, 4160-4165

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A novel strategy towards the synthesis of orthogonally functionalised 4-aminoglycosides

L. J. van den Bos, J. D.C. Codée, J. H. van Boom, H. S. Overkleeft and G. A. van der Marel, Org. Biomol. Chem., 2003, 1, 4160 DOI: 10.1039/B309823K

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