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Triflation of N 3 -protected uridines (N-COPh, N-CH=CH-COOMe, N-NO 2 ) has been investigated. A stable 2'-O-triflyl derivative, that of N-nitro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine, has been isolated for the first time; by contrast to its congeners, it does not give cyclonucleoside-like intermediates. Nucleophilic attacks on this substrate lead to 2'β-substituted nucleosides...
A stable sulfate derivative of N-nitrouridine has been obtained for the first time; it shows synthetic advantages in relation to its α-epoxide counterpart. A new iodide-mediated denitration reaction is reported.
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