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Synthesis of 1-(2-Deoxy-2-C-fluoromethyl-β-D-arabinofuranosyl)cytosine as a potential antineoplastic agent

1994; Elsevier BV; Volume: 4; Issue: 5 Linguagem: Inglês

10.1016/s0960-894x(01)80187-6

1464-3405

Yuichi Yoshimura, Kazuko Saitoh, Noriyuki Ashida, Shinji Sakata, Akira Matsuda,

Amino Acid Enzymes and Metabolism

Abstract 2'-β-Spiroepoxy-uridine was obtained from the reaction between 2'-ketouridine and dimethylsulfoxonium methylid. The oxirine ring was cleaved by KFHF and the resulting tertiary hydroxyl group was removed by radical deoxygenenation using a t -methyl oxalyl-tributyltin hydride system to give 2-deoxy-2- C -fluoromethyl-1-β-D-arabinofuranosyl-uracil derivative 7 . Finally, the uracil moiety was converted to a cytosine counterpart, followed by deprotection to yield the title compound.