1-((2R,3R,4R,5S)-3-fluoro-4-(((((2R,3R,4R,5R)-4-fluoro-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methoxy)(methyl)amino)methyl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione | 200067-05-6

• 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,3R,4R,5S)-3-fluoro-4-(((((2R,3R,4R,5R)-4-fluoro-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methoxy)(methyl)amino)methyl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS: 200067-05-6
• 化学式: C₂₂H₂₉F₂N₅O₉
• 分子量: 545.497
• InChiKey: QFRULTGODGUBPC-ARONAYCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.99
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  181.11
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1-((2R,3R,4R,5S)-3-fluoro-4-(((((2R,3R,4R,5R)-4-fluoro-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methoxy)(methyl)amino)methyl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 在 吡啶 、 4-二甲氨基吡啶 、 二异丙基铵盐四氮唑 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-[[(2R,3R,4R,5R)-2-[[[(2S,3R,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]methyl-methylamino]oxymethyl]-4-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  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：

  1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-β-D-arabino-pentofuranosyl>thymine 在 吡啶 、 四丁基氟化铵 、 水 、 sodium cyanoborohydride 、 溶剂黄146 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.75h， 生成 1-((2R,3R,4R,5S)-3-fluoro-4-(((((2R,3R,4R,5R)-4-fluoro-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methoxy)(methyl)amino)methyl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-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