Issue 5, 2003
From the journal:

Organic & Biomolecular Chemistry

Bicyclic nucleosides; stereoselective dihydroxylation and 2′-deoxygenation†

Jacob Ravn,a   Morten Freitaga  and  Poul Nielsen*a  

* Corresponding authors

a Nucleic Acid Center, Department of Chemistry, University of Southern Denmark, 5230 Odense M, Denmark
E-mail: pon@chem.sdu.dk

Abstract

A series of polyhydroxylated bicyclic nucleoside derivatives is approached applying stereoselective dihydroxylation reactions. Three out of four isomeric and protected products were obtained after the stereoselectivity of dihydroxylation has been completely inverted comparing a bicyclic nucleoside with a tricyclic furanose substrate. A corresponding 2′-deoxynucleoside derivative has been obtained after an optimized deoxygenation procedure.

Graphical abstract: Bicyclic nucleosides; stereoselective dihydroxylation and 2′-deoxygenation

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Article information

DOI
https://doi.org/10.1039/B210439C
Article type
Paper
Submitted
30 Oct 2002
Accepted
16 Jan 2003
First published
11 Feb 2003

Org. Biomol. Chem., 2003,1, 811-816

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Bicyclic nucleosides; stereoselective dihydroxylation and 2′-deoxygenation

J. Ravn, M. Freitag and P. Nielsen, Org. Biomol. Chem., 2003, 1, 811 DOI: 10.1039/B210439C

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