Coupling reaction of 2-substituted-6-methyl-4(3H)-pyrimidinones (la,b) with I-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.
M., R., Petricci, E., Corelli, F., Botta, M. (2007). Stereoselective Synthesis of N1-6-Methyluridine and Related 2-Substituted Analogues. HETEROCYCLES, 72, 79-83 [10.3987/COM-06-S(K)3].
Stereoselective Synthesis of N1-6-Methyluridine and Related 2-Substituted Analogues
PETRICCI, ELENA;CORELLI, FEDERICO;BOTTA, MAURIZIO
2007-01-01
Abstract
Coupling reaction of 2-substituted-6-methyl-4(3H)-pyrimidinones (la,b) with I-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.
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https://hdl.handle.net/11365/34710
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