N3-[(ethoxycarbonyl)-phosphonomethyl]uridine | 1357487-13-8

• 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: N3-[(ethoxycarbonyl)-phosphonomethyl]uridine
• CAS: 1357487-13-8
• 化学式: C₁₃H₁₉N₂O₁₁P
• 分子量: 410.274
• InChiKey: FQSYKOHYFIDZBP-FFLVSVRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.14
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  197.75
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  N3-[diethyl(ethoxycarbonyl)phosphonomethyl]-2',3'-O-isopropylidene uridine 在 三甲基溴硅烷 、 水 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 N3-[(carboxyl)phosphonomethyl]uridine 、 N3-[(ethoxycarbonyl)-phosphonomethyl]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

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.