diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonate | 651718-80-8

• 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: diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonate
• 英文别名: [(3R)-3-[[diethoxy(oxido)phosphaniumyl]-difluoromethyl]-5-phenylmethoxypentoxy]-tri(propan-2-yl)silane
• CAS: 651718-80-8
• 化学式: C₂₆H₄₇F₂O₅PSi
• 分子量: 536.712
• InChiKey: JWICCKGOZSFPBM-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.58
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]ethyl}butylphosphonate 在 palladium on activated charcoal 吡啶 、 偶氮二甲酸二异丙酯 、 氢气 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 66.0h， 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：

  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 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.25h， 生成 diethyl (2R)-4-(benzyloxy)-1,1-difluoro-2-{2-[(triisopropylsilyl)oxy]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

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.