[(2R,3R,4R,5R)-4-benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-2-[(5-iodo-2,4-dioxopyrimidin-1-yl)methyl]oxolan-3-yl] benzoate | 151576-02-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: [(2R,3R,4R,5R)-4-benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-2-[(5-iodo-2,4-dioxopyrimidin-1-yl)methyl]oxolan-3-yl] benzoate
• CAS: 151576-02-2
• 化学式: C₂₇H₂₁IN₄O₉
• 分子量: 672.39
• InChiKey: AAPYHNRQGAQPSW-KTDPBYDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  161
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-4-benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-2-[(5-iodo-2,4-dioxopyrimidin-1-yl)methyl]oxolan-3-yl] benzoate 在 palladium on activated charcoal sodium hydroxide 、 氨 、 氢气 作用下， 以 甲醇 为溶剂， 生成 5'-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5'-deoxy-uridine
  参考文献：
  名称：

  A novel synthesis of “double headed” nucleosides “reversed” nucleosides

  摘要：

  The ''double headed' nucleosides 10, 11 and 13 bearing pyrimidine or purine bases attached on C-1 and C-5 positions of single ribose unit have been synthesized following a new synthetic strategy. The strategy rests on the introduction of the first nucleo base at C-5 position of the ribose unit giving 'reversed' nucleoside and the subsequent attachment of the second base at C-1 position of the ribose, by classical glycosylation reaction. This order of the base attachments gave much better yields on the ''double headed' nucleosides then previously known C-1 then C-5 order of attachments.

  DOI：

  10.1016/s0040-4039(00)74067-6
• 作为产物：
  描述：

  尿嘧啶 、 [(2R,3R,4R)-5-acetyloxy-4-benzoyloxy-2-[(5-iodo-2,4-dioxopyrimidin-1-yl)methyl]oxolan-3-yl] benzoate 在 苯磺酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 生成 [(2R,3R,4R,5R)-4-benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-2-[(5-iodo-2,4-dioxopyrimidin-1-yl)methyl]oxolan-3-yl] benzoate
  参考文献：
  名称：

  A novel synthesis of “double headed” nucleosides “reversed” nucleosides

  摘要：

  The ''double headed' nucleosides 10, 11 and 13 bearing pyrimidine or purine bases attached on C-1 and C-5 positions of single ribose unit have been synthesized following a new synthetic strategy. The strategy rests on the introduction of the first nucleo base at C-5 position of the ribose unit giving 'reversed' nucleoside and the subsequent attachment of the second base at C-1 position of the ribose, by classical glycosylation reaction. This order of the base attachments gave much better yields on the ''double headed' nucleosides then previously known C-1 then C-5 order of attachments.

  DOI：

  10.1016/s0040-4039(00)74067-6