二乙基(2R)-4-[(二乙氧基磷酰基)氧基]-1,1-二氟-2-(2-羟乙基)丁基膦酸酯 | 651718-83-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 中文名称: 二乙基(2R)-4-[(二乙氧基磷酰基)氧基]-1,1-二氟-2-(2-羟乙基)丁基膦酸酯
• 英文名称: diethyl (2R)-4-[(diethoxyphosphoryl)oxy]-1,1-difluoro-2-(2-hydroxyethyl)butylphosphonate
• CAS: 651718-83-1
• 化学式: C₁₄H₃₀F₂O₈P₂
• 分子量: 426.332
• InChiKey: UKUKLPGUCJJSBT-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  26.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  二乙基(2R)-4-[(二乙氧基磷酰基)氧基]-1,1-二氟-2-(2-羟乙基)丁基膦酸酯 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.0h， 生成 diethyl (2R)-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：

  5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-1-O-(triisopropylsilyl)-D-erythro-pentitol 在 palladium on activated charcoal 吡啶 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 68.25h， 生成 二乙基(2R)-4-[(二乙氧基磷酰基)氧基]-1,1-二氟-2-(2-羟乙基)丁基膦酸酯
  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