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Communication | Special issue | Vol 72, No. 1, 2007, pp.79-83
Published online, 25th August, 2006
DOI: 10.3987/COM-06-S(K)3
Stereoselective Synthesis of N1-6-Methyluridine and Related 2-Substituted Analogues

Marco Radi, Elena Petricci, Federico Corelli, and Maurizio Botta*

*Dipartimento Farmaco Chimico Tecnologico, Università di Siena, Via Aldo Moro, 53100 Siena, Italy

Abstract

Coupling reaction of 2-substituted-6-methyl-4(3H)-pyrimidinones (1a,b) with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (ABR) afforded the corresponding N1-2,6-disubstituted nucleosides (2a,b) without any trace of the N3-isomer. The 2-methylthio-6-methyl derivative (2b) has then proved to be a key intermediate for the synthesis of N1-6-methyluridine (4) and the corresponding N1-2-amino-6-metyhl derivative (5), suggesting the possibility to obtain different 2,6-disubstituted derivatives by means of methylthio nucleophilic substitution. A successful solid phase application was also shown.