[(2R,3R,4R,5R)-5-(2-acetamido-6-oxo-3H-purin-9-yl)-2-[[[(2R,3R,4R,5R)-5-(2-acetamido-6-oxo-3H-purin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-fluorooxolan-3-yl]oxy-methoxyphosphoryl]oxymethyl]-4-(2-methylpropanoyloxy)oxolan-3-yl] 2-methylpropanoate | 514830-09-2

• 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: [(2R,3R,4R,5R)-5-(2-acetamido-6-oxo-3H-purin-9-yl)-2-[[[(2R,3R,4R,5R)-5-(2-acetamido-6-oxo-3H-purin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-fluorooxolan-3-yl]oxy-methoxyphosphoryl]oxymethyl]-4-(2-methylpropanoyloxy)oxolan-3-yl] 2-methylpropanoate
• CAS: 514830-09-2
• 化学式: C₅₄H₆₀FN₁₀O₁₇P
• 分子量: 1171.1
• InChiKey: OPJHNHKEMIYISY-RKCYUYOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  83.0
• 可旋转键数：
  22.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  328.85
• 氢给体数：
  4.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-5-(2-acetamido-6-oxo-3H-purin-9-yl)-2-[[[(2R,3R,4R,5R)-5-(2-acetamido-6-oxo-3H-purin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-fluorooxolan-3-yl]oxy-methoxyphosphoryl]oxymethyl]-4-(2-methylpropanoyloxy)oxolan-3-yl] 2-methylpropanoate 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以72%的产率得到[(2R,3R,4R,5R)-5-(2-acetamido-6-oxo-3H-purin-9-yl)-2-[[[(2R,3R,4R,5R)-5-(2-acetamido-6-oxo-3H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-yl]oxy-methoxyphosphoryl]oxymethyl]-4-(2-methylpropanoyloxy)oxolan-3-yl] 2-methylpropanoate
  参考文献：
  名称：

  SYNTHESIS of 2′-DEOXY-2′-FLUOROGUANYL-(3′,5′)-GUANOSINE

  摘要：

  The protected analogue of 2-amnio-6-chloropurine arabinoside (3b) was subjected to reaction with diethylaminosulfur trifluoride (DAST) and subsequently treated with NaOAc in Ac2O/AcOH to give N-2, O-3', O-5'-triacetyl-2'-deoxy-2'-fluoroguanosine (5a). After deacetylation of the sugar moiety and protection of 5'-OH by a 4,4'-dimethoxytrityl group, this nucleoside component was converted to 2'-deoxy-2-fluoroguanyl-(3',5')-guanosine (6c, GfpG).

  DOI：

  10.1081/ncn-120016479
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 在 吡啶 、 四氮唑 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 6.0h， 生成 [(2R,3R,4R,5R)-5-(2-acetamido-6-oxo-3H-purin-9-yl)-2-[[[(2R,3R,4R,5R)-5-(2-acetamido-6-oxo-3H-purin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-fluorooxolan-3-yl]oxy-methoxyphosphoryl]oxymethyl]-4-(2-methylpropanoyloxy)oxolan-3-yl] 2-methylpropanoate
  参考文献：
  名称：

  SYNTHESIS of 2′-DEOXY-2′-FLUOROGUANYL-(3′,5′)-GUANOSINE

  摘要：

  The protected analogue of 2-amnio-6-chloropurine arabinoside (3b) was subjected to reaction with diethylaminosulfur trifluoride (DAST) and subsequently treated with NaOAc in Ac2O/AcOH to give N-2, O-3', O-5'-triacetyl-2'-deoxy-2'-fluoroguanosine (5a). After deacetylation of the sugar moiety and protection of 5'-OH by a 4,4'-dimethoxytrityl group, this nucleoside component was converted to 2'-deoxy-2-fluoroguanyl-(3',5')-guanosine (6c, GfpG).

  DOI：

  10.1081/ncn-120016479