1-O-triisopropylsilyl-2-deoxy-2,2-difluoro-3-O-benzoyl-D-arabinofuranose | 1430067-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-triisopropylsilyl-2-deoxy-2,2-difluoro-3-O-benzoyl-D-arabinofuranose
• 英文别名: [(2R,3R)-4,4-difluoro-2-(hydroxymethyl)-5-tri(propan-2-yl)silyloxyoxolan-3-yl] benzoate
• CAS: 1430067-49-4
• 化学式: C₂₁H₃₂F₂O₅Si
• 分子量: 430.564
• InChiKey: XTZMWKQJCJVHSJ-KUBVQFIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-脱氧-2,2-二氟戊呋喃糖-1-酮 3,5-二安息香酸盐 在 2,6-二甲基吡啶 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 1-O-triisopropylsilyl-2-deoxy-2,2-difluoro-5-O-benzoyl-D-arabinofuranose 、 1-O-triisopropylsilyl-2-deoxy-2,2-difluoro-3,5-di-O-benzoyl-α-D-arabinofuranose 、 1-O-triisopropylsilyl-2-deoxy-2,2-difluoro-3,5-di-O-benzoyl-β-D-arabinofuranose 、 1-O-triisopropylsilyl-2-deoxy-2,2-difluoro-3-O-benzoyl-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

文献信息

• Synthesis and biological evaluation of prodrugs of 2-fluoro-2-deoxyribose-1-phosphate and 2,2-difluoro-2-deoxyribose-1-phosphate
  作者：Nadege Hamon、Maurizio Quintiliani、Jan Balzarini、Christopher McGuigan

  DOI：10.1016/j.bmcl.2013.02.117

  日期：2013.5

  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.