N3-methoxyethoxymethyl-2',3'-O-isopropylidene uridine | 1357486-95-3

• 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: N3-methoxyethoxymethyl-2',3'-O-isopropylidene uridine
• CAS: 1357486-95-3
• 化学式: C₁₆H₂₄N₂O₈
• 分子量: 372.375
• InChiKey: SYBDJPBQDFVFEC-FMKGYKFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.96
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  110.38
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-diazo-2-(diethoxyphosphoryl)acetate 、 N3-methoxyethoxymethyl-2',3'-O-isopropylidene uridine 在 dirhodium tetraacetate 作用下， 以 苯 为溶剂， 以32%的产率得到N3-methoxyethoxymethyl-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
• 作为产物：
  描述：

  5'-O-benzoyl-2',3'-O-isopropylidene uridine 在 甲醇 、 苄基三乙基氯化铵 、 氨 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 N3-methoxyethoxymethyl-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