A seven-step synthesis of 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose, a versatile intermediate in the synthesis of chemotherapeutically important nucleosides, was achieved from 1,2:5,6-di-O-isopropylidene-3-O-tosyl-alpha-D-allofuranose. The crucial steps were the fluorination by use of potassium fluoride in acetamide and the conversion of 6-O-benzoyl-3-deoxy-3-fluoro-D-glucofuranose into 5-O-benzoyl-2-deoxy-2-fluoro-3-O-formyl-D-arabinofuranose by periodate oxidation. Also described is the synthesis of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosine. This procedure affords good overall yields of products without formation of undesirable, isomeric intermediates and is suitable for large-scale preparations.

中文翻译：

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2-脱氧-2-氟-D-阿拉伯呋喃糖衍生物的实用合成。

从1，开始，合成了1,3-二-O-乙酰基-5-O-苯甲酰基-2-脱氧-2-氟-D-阿拉伯呋喃糖的七步合成方法，该中间体是化学治疗中重要的核苷合成中的通用中间体。 2：5，6-二-O-异亚丙基-3-O-甲苯磺酰基-α-D-呋喃糖。关键步骤是在乙酰胺中使用氟化钾进行氟化，并将6-O-苯甲酰基-3-脱氧-3-氟-D-葡萄糖呋喃糖转化为5-O-苯甲酰基-2-脱氧-2-氟-3 -O-甲酰基-D-阿拉伯呋喃糖经高碘酸盐氧化。还描述了1-（2-脱氧-2-氟-β-D-阿拉伯呋喃糖基）胞嘧啶的合成。该方法提供了良好的产物总产率，而没有形成不期望的异构中间体，并且适合于大规模制备。