5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]thymidine | 1357487-04-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]thymidine
• CAS: 1357487-04-7
• 化学式: C₁₈H₂₉N₂O₁₀P
• 分子量: 464.409
• InChiKey: QQXFQAMTTJQYPY-FILYFMJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  155.38
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 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， 反应 12.0h， 生成 5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]thymidine 、 3'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]thymidine 、 3',5'-O-bis[diethyl(ethoxycarbonyl)phosphonomethyl]thymidine
  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

文献信息

• Development of O–H insertion for the attachment of phosphonates to nucleosides; synthesis of α-carboxy phosphononucleosides
  作者：Isabelle Hladezuk、Veronique Chastagner、Stuart G. Collins、Stephen J. Plunkett、Alan Ford、Sebastien Debarge、Anita R. Maguire

  DOI：10.1016/j.tet.2011.12.077

  日期：2012.2

  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.