5'-O-phthalimido-2'-fluorothymidine | 171176-06-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-phthalimido-2'-fluorothymidine
• 英文别名: 2-[[(2R,3R,4R,5R)-4-fluoro-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]isoindole-1,3-dione
• CAS: 171176-06-0
• 化学式: C₁₈H₁₆FN₃O₇
• 分子量: 405.339
• InChiKey: RRTHHBJCKNCIDM-HPTBWKMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.33
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  130.93
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5'-O-phthalimido-2'-fluorothymidine 在 咪唑 、 甲基肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 5'-O-amino-3'-O-tert-butyldiphenylsilyl-2'-fluorothymidine
  参考文献：
  名称：

  Synthesis of 2′‐Substituted MMI Linked Nucleosidic Dimers: An Optimization Study in Search of High Affinity Oligonucleotides for Use in Antisense Constructs

  摘要：

  The synthesis of a series of methylene(methylimino) (MMI) linked oligodeoxyribonucleotide dimers modified at the 2'-position with fluoro and/or methoxy groups and their incorporation into different sequences has been accomplished. From these dimers, his 2'-OMe MMI dimer was selected for further studies based on its synthetic accessibility and the increased thermodynamic stability conferred upon oligonucleotides incorporating this modification.

  DOI：

  10.1081/ncn-120028337
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 2’-氟胸苷 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到5'-O-phthalimido-2'-fluorothymidine
  参考文献：
  名称：

  Synthesis of 2′‐Substituted MMI Linked Nucleosidic Dimers: An Optimization Study in Search of High Affinity Oligonucleotides for Use in Antisense Constructs

  摘要：

  The synthesis of a series of methylene(methylimino) (MMI) linked oligodeoxyribonucleotide dimers modified at the 2'-position with fluoro and/or methoxy groups and their incorporation into different sequences has been accomplished. From these dimers, his 2'-OMe MMI dimer was selected for further studies based on its synthetic accessibility and the increased thermodynamic stability conferred upon oligonucleotides incorporating this modification.

  DOI：

  10.1081/ncn-120028337