Synthesis of 6,5'-Cyclo-5'-deoxy-5'(R and S)-(2-hydroxyethyl)-uridmes (Nucleosides and Nucleotides. LXXIII)(Organic,Chemical)

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Oxidation of 6,5'-cycto-5'-deoxy-2',3'-O-isopropylideneuridine with selenium dioxide gave the 5'-oxo derivative, which was converted to the 5'-ethoxycarbonylmethylidene derivative (3). Reduction of 3 afforded, after deprotection, the title compounds (6, R and S). The base-catalyzed epimerization of 6 at the 5'-position was observed, and the equilibrium was in favor of the (R)-epimer.

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