二乙基(2S)-4-(苄氧基)-1,1-二氟-2-(2-羟乙基)丁基膦酸酯 | 651718-81-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 二乙基(2S)-4-(苄氧基)-1,1-二氟-2-(2-羟乙基)丁基膦酸酯
• 英文名称: diethyl (2S)-4-(benzyloxy)-1,1-difluoro-2-(2-hydroxyethyl)butylphosphonate
• 英文别名: (3S)-3-[diethoxyphosphoryl(difluoro)methyl]-5-phenylmethoxypentan-1-ol
• CAS: 651718-81-9
• 化学式: C₁₇H₂₇F₂O₅P
• 分子量: 380.369
• InChiKey: QBEFZJLWQHZKFF-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  二乙基(2S)-4-(苄氧基)-1,1-二氟-2-(2-羟乙基)丁基膦酸酯 在 palladium on activated charcoal 吡啶 、 偶氮二甲酸二异丙酯 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 diethyl (2R)-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
• 作为产物：
  描述：

  (2S,3S)-[(2-benzyloxymethyl-5-oxotetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester 在 2,6-二甲基吡啶 、 锂硼氢 、 硼酸三甲酯 、 偶氮二异丁腈 、 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 44.25h， 生成 二乙基(2S)-4-(苄氧基)-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

文献信息

• Synthesis of acyclic nucleotide analogues possessing a difluoromethylene phosphonyl group at the side chain
  作者：Tetsuo Murano、Yoko Yuasa、Hirokuni Kobayakawa、Tsutomu Yokomatsu、Shiroshi Shibuya

  DOI：10.1016/j.tet.2003.10.064

  日期：2003.12

  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.