1-[(2R,4R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[[[(2R,3R,4R,5R)-4-fluoro-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-methylamino]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione | 171176-13-9

• 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: 1-[(2R,4R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[[[(2R,3R,4R,5R)-4-fluoro-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-methylamino]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 171176-13-9
• 化学式: C₃₈H₄₈FN₅O₉Si
• 分子量: 765.911
• InChiKey: JSMRIEYXPZHVEF-HKHARCQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  54.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  170.11
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1-[(2R,4R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[[[(2R,3R,4R,5R)-4-fluoro-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-methylamino]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到1-[(2R,4R,5S)-4-[[[(2R,3R,4R,5R)-4-fluoro-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-methylamino]methyl]-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  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：

  5'-O-amino-2'-fluorothymidine 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.5h， 生成 1-[(2R,4R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[[[(2R,3R,4R,5R)-4-fluoro-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-methylamino]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  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