Issue 2, 2010
From the journal:

Organic & Biomolecular Chemistry

Diastereoselective synthesis of (±)-1′,4′-dimethyluridine†

Guillaume Sautrey,a   Damien Bourgeois*a  and  Christian Périgauda  

* Corresponding authors

a Institut des Biomolécules Max Mousseron (IBMM) UMR 5247 CNRS-UM 1-UM 2 Université Montpellier 2, CC 1705, Place Eugène Bataillon, Montpellier Cedex 5, France
E-mail: damien.bourgeois@univ-montp2.fr
Fax: +33 (0)4 67 04 20 29
Tel: +33 (0)4 67 14 38 79

Abstract

The de novo synthesis of racemic 1′,4′-dimethyluridine was accomplished in 12 steps starting from 2,5-dimethylfuran and vinylene carbonate. Key steps of the sequence include the stereoconvergent preparation of a meso diacid, and a stereoselective glycosylation without neighboring group participation. Such 1′,4′-disubstituted ribonucleoside analogues are undisclosed compounds, which may present interesting biological activities.

Graphical abstract: Diastereoselective synthesis of (±)-1′,4′-dimethyluridine

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Article information

DOI
https://doi.org/10.1039/B912411J
Article type
Paper
Submitted
23 Jun 2009
Accepted
24 Sep 2009
First published
26 Oct 2009

Org. Biomol. Chem., 2010,8, 378-383

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Diastereoselective synthesis of (±)-1′,4′-dimethyluridine

G. Sautrey, D. Bourgeois and C. Périgaud, Org. Biomol. Chem., 2010, 8, 378 DOI: 10.1039/B912411J

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