diethyl (2S)-4-(6-chloro-9H-purin-9-yl)-2-{2-[(diethoxyphosphoryl)oxy]ethyl}-1,1-difluorobutylphosphonate | 651718-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: diethyl (2S)-4-(6-chloro-9H-purin-9-yl)-2-{2-[(diethoxyphosphoryl)oxy]ethyl}-1,1-difluorobutylphosphonate
• CAS: 651718-88-6
• 化学式: C₁₉H₃₁ClF₂N₄O₇P₂
• 分子量: 562.875
• InChiKey: XAYBLFKUWJXUIJ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  35.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  123.89
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  甲胺 、 diethyl (2S)-4-(6-chloro-9H-purin-9-yl)-2-{2-[(diethoxyphosphoryl)oxy]ethyl}-1,1-difluorobutylphosphonate 以 水 为溶剂， 反应 4.0h， 以86%的产率得到diethyl (2S)-4-[(diethoxyphosphoryl)oxy]-1,1-difluoro-2-{2-[6-(methylamino)-9H-purin-9-yl]ethyl}butylphosphonate
  参考文献：
  名称：

  Synthesis of acyclic nucleotide analogues possessing a difluoromethylene phosphonyl group at the side chain

  摘要：

  A synthetic approach to a new type of acyclic nucleotide analogues 8 and 9 was examined. The design was based on acyclic modification of MRS 2179, a P2Y(1)-antagonist, and replacement of one of two phosphate groups characterized by MRS 2179 with an isosteric difluoromethylenephosphonyl group. The nucleotide analogues 8 and 9 were enantio-divergently prepared as their ester-protecting derivatives from a highly differentiated 1,5-pentanediol derivative possessing a difluoromethylenephosphonyl group at the 3-position. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.064
• 作为产物：
  描述：

  O,O-diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonothioate 在 palladium on activated charcoal 吡啶 、 偶氮二甲酸二异丙酯 、 氢气 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 66.25h， 生成 diethyl (2S)-4-(6-chloro-9H-purin-9-yl)-2-{2-[(diethoxyphosphoryl)oxy]ethyl}-1,1-difluorobutylphosphonate
  参考文献：
  名称：

  Synthesis of acyclic nucleotide analogues possessing a difluoromethylene phosphonyl group at the side chain

  摘要：

  A synthetic approach to a new type of acyclic nucleotide analogues 8 and 9 was examined. The design was based on acyclic modification of MRS 2179, a P2Y(1)-antagonist, and replacement of one of two phosphate groups characterized by MRS 2179 with an isosteric difluoromethylenephosphonyl group. The nucleotide analogues 8 and 9 were enantio-divergently prepared as their ester-protecting derivatives from a highly differentiated 1,5-pentanediol derivative possessing a difluoromethylenephosphonyl group at the 3-position. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.064