β-1-O-triisopropylsilyl-2-deoxy-2-fluoro-3,5-di-O-benzyloxycarbonyl-D-arabinofuranose | 1430067-44-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-1-O-triisopropylsilyl-2-deoxy-2-fluoro-3,5-di-O-benzyloxycarbonyl-D-arabinofuranose
• CAS: 1430067-44-9
• 化学式: C₃₀H₄₁FO₈Si
• 分子量: 576.735
• InChiKey: FQBPGIQMBGHMRX-GCFVYEKYSA-N

反应信息

• 作为产物：
  描述：

  1-O-triisopropylsilyl-2-deoxy-2-fluoro-D-arabinofuranose 、 氯甲酸苄酯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 α-1-O-triisopropylsilyl-2-deoxy-2-fluoro-3,5-di-O-benzyloxycarbonyl-D-arabinofuranose 、 β-1-O-triisopropylsilyl-2-deoxy-2-fluoro-3,5-di-O-benzyloxycarbonyl-D-arabinofuranose
  参考文献：
  名称：

  Synthesis and biological evaluation of prodrugs of 2-fluoro-2-deoxyribose-1-phosphate and 2,2-difluoro-2-deoxyribose-1-phosphate

  摘要：

  We report in this Letter the synthesis of prodrugs of 2-fluoro-2-deoxyarabinose-1-phosphate and 2,2-difluoro-2-deoxyribose-1-phosphate. We demonstrate the difficulty of realising a phosphorylation step on the anomeric position of 2-deoxyribose, and we discover that introduction of fluorine atoms on the 2 position of 2-deoxyribose enables the phosphorylation step: in fact, the stability of the prodrugs increases with the degree of 2-fluorination. Stability studies of produgs of 2-fluoro-2-deoxyribose-1-phosphate and 2,2-difluoro-2-deoxyribose-1-phosphate in acidic and neutral conditions were conducted to confirm our observation. Biological evaluation of prodrugs of 2,2-difluoro-2-deoxyribose-1-phosphate for antiviral and cytotoxic activity is reported. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.02.117