Nucleosides. II. Direct Synthesis of 5-Substituted 2', 5'-Anhydro-1-β-D-arabinofuranosyluracils from Uridine Derivatives

K HIROTA, Y KITADE, T TOMISHI…

Index: Hirota; Kitade; Tomishi; Maki Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 10 p. 4212 - 4215

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Abstract

Reaction of 5-substituted 2', 5'-dichloro-2', 5'-dideoxyuridines (1a-d) with methanolic sodium hydroxide under reflux afforded the corresponding 5-substituted 2', 5'-anhydro-1-β-D- arabino-furanosyluracils (3a-d) in high yield. On the other hand, reaction of 5-substituted uridines (5a-d) with the Vilsmeier-Haack reagent (POCl 3/DMF) followed by treatment with methanolic sodium hydroxide under reflux led directly to the formation of the ...