2-deoxy-2,2-difluoro-3,5-di-O-benzyloxycarbonyl-α-D-arabinofuranose | 1430067-54-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2,2-difluoro-3,5-di-O-benzyloxycarbonyl-α-D-arabinofuranose
• 英文别名: benzyl [(2R,3R,5S)-4,4-difluoro-5-hydroxy-2-(phenylmethoxycarbonyloxymethyl)oxolan-3-yl] carbonate
• CAS: 1430067-54-1
• 化学式: C₂₁H₂₀F₂O₈
• 分子量: 438.382
• InChiKey: MOYGSNYMJFXMAQ-KURKYZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1-O-triiospropylsilyl-2-deoxy-2,2-difluoro-3,5-di-O-benzyloxycarbonyl-D-arabinofuranose 在 pyridine hydrofluoride 作用下， 以 吡啶 为溶剂， 反应 16.0h， 以25%的产率得到
  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