2',3'-di-O-benzoyl-5'-O-{[(bis-ethyloxyphosphorylmethyl)ethyloxyphosphorylmethyl]methyloxyphosphoryl}-N³-benzoyluridine | 911135-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',3'-di-O-benzoyl-5'-O-{[(bis-ethyloxyphosphorylmethyl)ethyloxyphosphorylmethyl]methyloxyphosphoryl}-N³-benzoyluridine
• 英文别名: [(2R,3R,4R,5R)-5-(3-benzoyl-2,4-dioxopyrimidin-1-yl)-4-benzoyloxy-2-[[[diethoxyphosphorylmethyl(ethoxy)phosphoryl]methyl-methoxyphosphoryl]oxymethyl]oxolan-3-yl] benzoate
• CAS: 911135-76-7
• 化学式: C₃₉H₄₅N₂O₁₆P₃
• 分子量: 890.711
• InChiKey: PDOSKAQSIMZTHC-HQAFAMSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  60
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  217
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2',3'-di-O-benzoyl-5'-O-{[(bis-ethyloxyphosphorylmethyl)ethyloxyphosphorylmethyl]methyloxyphosphoryl}-N³-benzoyluridine 在 三甲基溴硅烷 、 ammonium hydroxide 、 Dowex 50 Na⁽¹⁺⁾ 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 108.0h， 以62%的产率得到5'-O-{[(dihydroxy-phosphorylmethyl)hydroxyphosphorylmethyl]hydroxyphosphoryl}uridine tetrasodium salt
  参考文献：
  名称：

  An Unsymmetrical Approach to the Synthesis of Bismethylene Triphosphate Analogues

  摘要：

  A protected, unsymmetrical bismethylene triphosphate analogue was prepared by sequential Michaelis-Arbuzov reactions on ethyl bis(halomethyl) phosphinates. This species was monodeprotected at one of the terminal phosphonate groups in high yield. The resulting monodeprotected compound was used to achieve the first syntheses of the bismethylene triphosphate analogues of UTP and CTP.

  DOI：

  10.1021/ol0615432
• 作为产物：
  描述：

  (iodomethylethoxyphosphinoylmethyl)phosphonic acid diethyl ester 在 potassium cyanide 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 2',3'-di-O-benzoyl-5'-O-{[(bis-ethyloxyphosphorylmethyl)ethyloxyphosphorylmethyl]methyloxyphosphoryl}-N³-benzoyluridine
  参考文献：
  名称：

  An Unsymmetrical Approach to the Synthesis of Bismethylene Triphosphate Analogues

  摘要：

  A protected, unsymmetrical bismethylene triphosphate analogue was prepared by sequential Michaelis-Arbuzov reactions on ethyl bis(halomethyl) phosphinates. This species was monodeprotected at one of the terminal phosphonate groups in high yield. The resulting monodeprotected compound was used to achieve the first syntheses of the bismethylene triphosphate analogues of UTP and CTP.

  DOI：

  10.1021/ol0615432

文献信息

• An Unsymmetrical Approach to the Synthesis of Bismethylene Triphosphate Analogues
  作者：Scott D. Taylor、Farzad Mirzaei、Stephen L. Bearne

  DOI：10.1021/ol0615432

  日期：2006.9

  A protected, unsymmetrical bismethylene triphosphate analogue was prepared by sequential Michaelis-Arbuzov reactions on ethyl bis(halomethyl) phosphinates. This species was monodeprotected at one of the terminal phosphonate groups in high yield. The resulting monodeprotected compound was used to achieve the first syntheses of the bismethylene triphosphate analogues of UTP and CTP.