O,O-diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonothioate | 651718-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O,O-diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonothioate
• CAS: 651718-79-5
• 化学式: C₂₆H₄₇F₂O₄PSSi
• 分子量: 552.779
• InChiKey: JKDKZCLRQMCIDK-RUZDIDTESA-N

物化性质

• 沸点：
  527.7±60.0 °C(predicted)
• 密度：
  1.052±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.77
• 重原子数：
  35.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  O,O-diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonothioate 在 palladium on activated charcoal 吡啶 、 氢气 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.25h， 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
• 作为产物：
  描述：

  5-O-benzyl-2,3-dideoxy-3-[(diethoxyphosphorothioyl)(difluoro)methyl]-4-O-(1H-imidazol-1-yl-carbonothioyl)-1-O-(triisopropylsilyl)-D-erythro-pentitol 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以91%的产率得到O,O-diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonothioate
  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