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

Guillaume Sautrey; Damien Bourgeois; Christian Périgaud

doi:10.1039/B912411J

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Organic & Biomolecular Chemistry

Issue 2, 2010

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

Guillaume Sautrey , Damien Bourgeois and Christian Périgaud

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

DOI: 10.1039/B912411J
Received 23 Jun 2009, Accepted 24 Sep 2009
First published on the web 26 Oct 2009

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Abstract
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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.

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¹H and ¹³C NMR spectra for all new compounds
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Organic & Biomolecular Chemistry

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

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