[(2R,3S,5R)-3-acetyloxy-5-[5-[anilino(dimethoxyphosphoryl)methyl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate | 1245614-45-2

• 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: [(2R,3S,5R)-3-acetyloxy-5-[5-[anilino(dimethoxyphosphoryl)methyl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 1245614-45-2
• 化学式: C₂₂H₂₈N₃O₁₀P
• 分子量: 525.452
• InChiKey: REBKBZGBLIPLLU-BSWYJCKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  亚磷酸二甲酯 、 苯胺 、 3',5'-di-O-acetyl-2'-deoxy-5-formyluridine 反应 2.0h， 以86%的产率得到[(2R,3S,5R)-3-acetyloxy-5-[5-[anilino(dimethoxyphosphoryl)methyl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate
  参考文献：
  名称：

  Solvent-Free Synthesis of Pyrimidine Nucleoside-Aminophosphonate Hybrids and Their Biological Activity Evaluation

  摘要：

  A novel and highly efficient one-pot three-component synthesis of -aminophosphonates under neat condition was developed. By employing this method, hybrid compounds of aminophosphonate with pyrimidine nucleosides were synthesized in good to excellent yields starting from 5-formyl-2'-deoxyuridine, aniline and dimethyl phosphite. The antiviral and antileishmanial activities of these novel hybrid compounds were also studied but none were found to be active.

  DOI：

  10.1080/15257770.2010.496281

文献信息

• An efficient and green preparation of 5-aminophosphonate substituted pyrimidine nucleosides under solvent-free conditions
  作者：Xin Ying Zhang、Ying Ying Qu、Xue Sen Fan

  DOI：10.1016/j.cclet.2010.04.037

  日期：2010.10

  An environmentally benign and highly efficient one-pot preparation of α-aminophosphonates under solvent-free conditions was developed. By employing this method, 5-aminophosphonate substituted pyrimidine nucleosides were synthesized in good to excellent yields starting from 5-formyl-2′-deoxyuridine, aniline and dimethylphosphite.

  开发了一种在无溶剂条件下对环境无害且高效的一锅法制备α-氨基膦酸酯的方法。通过使用该方法，以5-甲酰基-2'-脱氧尿苷，苯胺和亚磷酸二甲酯为起始原料，以良好的优良合成了5-氨基膦酸酯取代的嘧啶核苷。