Nucleosides. 102. Synthesis of some 3'-deoxy-3'-substituted arabinofuranosylpyrimidine nucleosides

The synthesis of some 3'-deoxy-3'-substituted arabinofuranosylcytosine (4a-d) and uracil (7a-d, 8a-d, X =Br, I, N3, SCN) nucleosides was accomplished by treatment of the requisite 2',3'-anhydrolyxofuranosylpyrimidine nucleoside (5,6a,b) with the appropriate ammonium salt in refluxing ethanol. Cleavage of the oxirane ring provided the desired 3'-deoxy-3'-substituted pyrimidine nucleosides (4a-d, 7a-d, and 8a-d). In vitro screening of compounds 4a-d, and 7a-d, with L5178Y cells in culture showed no significant inhibitory properties.