5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]-2',3'-O-isopropylidene uridine | 1357486-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]-2',3'-O-isopropylidene uridine
• 英文别名: ethyl 2-[[(3aR,4R,6R,6aR)-4-(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: 1357486-92-0
• 化学式: C₂₀H₃₁N₂O₁₁P
• 分子量: 506.447
• InChiKey: DWZXHLVTLLMAMO-NQRWXQSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5'-O-[diethyl(ethoxycarbonyl)phosphonomethyl]-2',3'-O-isopropylidene uridine 在 三甲基溴硅烷 、 水 、 氨 作用下， 以 乙腈 、 水 为溶剂， 以77%的产率得到5'-O-[(carboxyl)phosphonomethyl]uridine ammonium salt
  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：

  ethyl 2-diazo-2-(diethoxyphosphoryl)acetate 在 dirhodium tetraacetate 、 苯甲醇 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 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

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.