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Synthesis of 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodo [2-14C] uracil

✍ Scribed by J. E. Swigor; K. A. Pittman

Publisher
John Wiley and Sons
Year
1985
Tongue
French
Weight
232 KB
Volume
22
Category
Article
ISSN
0022-2135

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✦ Synopsis

The synthesis of t h e title canpound (7) is described. [2-14C] cytosine (I) is treated with an aqueous mixture of sodium bisulfite and sodium sulfate at 8OoC for 30 rnin. The resulting solid is then treated with aqueous sodiun hydroxide and passed through a cation exchange colunn, producing [ Z-14C] uracil (2). Iodionatim with iodic acid and iodine in acetic acid yielded 5-iOdO-P-l4C ]uracil (31 Treatment of (3) with hexamethyldisilazane formed the trimethylsilated pyrimidine. Condensation with 3-0-acetyl-5-0-benzoyl-2-deoxy-2-fluoro-D-arabinosyl bromide produced a mixture of a, 8 i s m e s . Separation by colunn chromatography and saponification with aqueous potassium carbonate yielded the title compound.

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