N6,N6-dibenzylformamidine-5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]-2',3'-O-isopropylidene adenosine | 1357486-91-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N6,N6-dibenzylformamidine-5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]-2',3'-O-isopropylidene adenosine
• CAS: 1357486-91-9
• 化学式: C₃₆H₄₅N₆O₉P
• 分子量: 736.762
• InChiKey: DWLWJSVOMLZCOL-CBBZKYNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  52.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  157.95
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  N6,N6-dibenzylformamidine-5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]-2',3'-O-isopropylidene adenosine 在 20% palladium hydroxide on charcoal 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以58%的产率得到5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]-2',3'-O-isopropylidene adenosine
  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：

  2',3'-异丙叉腺苷 、 二苄胺 在 Rh₂(CF₃CONH)₄ 作用下， 以 甲苯 、 苯 为溶剂， 反应 72.0h， 生成 N6,N6-dibenzylformamidine-5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]-2',3'-O-isopropylidene adenosine
  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