N3-benzoyl-5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]-2',3'-O-isopropylidene uridine | 1357486-96-4

• 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: N3-benzoyl-5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]-2',3'-O-isopropylidene uridine
• 英文别名: ethyl 2-[[(3aR,4R,6R,6aR)-4-(3-benzoyl-2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-2-[diethoxy(oxido)phosphaniumyl]acetate
• CAS: 1357486-96-4
• 化学式: C₂₇H₃₅N₂O₁₂P
• 分子量: 610.555
• InChiKey: MKKDOPNRSSSJTK-NXOVXLMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  162
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N3-benzoyl-5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]-2',3'-O-isopropylidene uridine 在 甲醇 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 12.0h， 以44%的产率得到5'-[diethyl(amido)phosphonomethoxy]-2',3'-O-isopropylidene uridine
  参考文献：
  名称：

  Development of O–H insertion for the attachment of phosphonates to nucleosides; synthesis of α-carboxy phosphononucleosides

  摘要：

  Development of rhodium catalysed O-H insertion reactions employing alpha-diazophosphonates with appropriately protected adenosine, uridine and thymidine derivatives is described. This synthetic methodology leads, following deprotection, to novel phosphononucleoside derivatives bearing a carboxylic acid moiety adjacent to the phosphonate. Protection strategies are critical to the success of the key O-H insertion. There are two important aspects: avoiding competing insertion pathways or catalyst poisoning, and being able to achieve deprotection without degradation of the phosphononucleosides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.077
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 在 dirhodium tetraacetate 、 对甲苯磺酰叠氮 、 potassium carbonate 作用下， 以 苯 为溶剂， 生成 N3-benzoyl-5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]-2',3'-O-isopropylidene uridine
  参考文献：
  名称：

  Development of O–H insertion for the attachment of phosphonates to nucleosides; synthesis of α-carboxy phosphononucleosides

  摘要：

  Development of rhodium catalysed O-H insertion reactions employing alpha-diazophosphonates with appropriately protected adenosine, uridine and thymidine derivatives is described. This synthetic methodology leads, following deprotection, to novel phosphononucleoside derivatives bearing a carboxylic acid moiety adjacent to the phosphonate. Protection strategies are critical to the success of the key O-H insertion. There are two important aspects: avoiding competing insertion pathways or catalyst poisoning, and being able to achieve deprotection without degradation of the phosphononucleosides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.077