2,4-dimethoxy-(2'S)-trans-5-<2',5'-dihydro-5'-<(triphenylmethoxy)methyl>-2'-furanyl>pyrimidine | 148440-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,4-dimethoxy-(2'S)-trans-5-<2',5'-dihydro-5'-<(triphenylmethoxy)methyl>-2'-furanyl>pyrimidine
• 英文别名: 2,4-dimethoxy-5-[(2S,5S)-5-(trityloxymethyl)-2,5-dihydrofuran-2-yl]pyrimidine
• CAS: 148440-99-7
• 化学式: C₃₀H₂₈N₂O₄
• 分子量: 480.563
• InChiKey: ACSYMUGRHMXZIO-BDYUSTAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-dimethoxy-(2'S)-trans-5-<2',5'-dihydro-5'-<(triphenylmethoxy)methyl>-2'-furanyl>pyrimidine 在 palladium on activated charcoal ammonium formate 作用下， 以 乙醇 为溶剂， 以94%的产率得到2,4-dimethoxy-(2'S)-trans-5--2'-furanyl>pyrimidine
  参考文献：
  名称：

  Enantio- and diastereoisomers of 2,4-dimethoxy-5-(2,3-dideoxy-5-O-tritylribofuranosyl)pyrimidine. 2',3'-Dideoxy pyrimidine C-nucleosides by palladium-mediated glycal-aglycon coupling

  摘要：

  Newly available enantiomeric 2,3-dideoxy glycals, (5S)- and (5R)-4,5-dihydro-5-[(triphenylmethoxy)-methyl] furans and 2,4-dimethoxy-5-iodopyrimidine undergo palladium-mediated coupling by two different, complementary procedures to form enantiomeric pairs of (2',3'-dideoxy-2',3'-didehydrofuranosyl)- and (2',3'-dideoxy-3',4'-didehydrofuranosyl)pyrimidine C-nucleosides. Stereoselective reductions of the carbohydrate unsaturations produce all four enantio- and diastereoisomers of 2,4-dimethoxy-5-(2,3-dideoxy-5-O-tritylribofuranosyl)pyrimidine. The facile two-step syntheses of 2',3'-deoxy C-nucleosides which involves preparation of a D-series C-nucleoside from an L-series glycal (and vice versa) represents a new strategy for C-nucleoside synthesis.

  DOI：

  10.1021/jo00061a034
• 作为产物：
  描述：

  (5S)-5-[(trityloxy)methyl]tetrahydro-2-furanone 在 palladium diacetate 四丁基氯化铵 、 sodium acetate 、 二异丁基氢化铝 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 2,4-dimethoxy-(2'S)-trans-5-<2',5'-dihydro-5'-<(triphenylmethoxy)methyl>-2'-furanyl>pyrimidine
  参考文献：
  名称：

  Enantio- and diastereoisomers of 2,4-dimethoxy-5-(2,3-dideoxy-5-O-tritylribofuranosyl)pyrimidine. 2',3'-Dideoxy pyrimidine C-nucleosides by palladium-mediated glycal-aglycon coupling

  摘要：

  Newly available enantiomeric 2,3-dideoxy glycals, (5S)- and (5R)-4,5-dihydro-5-[(triphenylmethoxy)-methyl] furans and 2,4-dimethoxy-5-iodopyrimidine undergo palladium-mediated coupling by two different, complementary procedures to form enantiomeric pairs of (2',3'-dideoxy-2',3'-didehydrofuranosyl)- and (2',3'-dideoxy-3',4'-didehydrofuranosyl)pyrimidine C-nucleosides. Stereoselective reductions of the carbohydrate unsaturations produce all four enantio- and diastereoisomers of 2,4-dimethoxy-5-(2,3-dideoxy-5-O-tritylribofuranosyl)pyrimidine. The facile two-step syntheses of 2',3'-deoxy C-nucleosides which involves preparation of a D-series C-nucleoside from an L-series glycal (and vice versa) represents a new strategy for C-nucleoside synthesis.

  DOI：

  10.1021/jo00061a034

文献信息

• Enantio- and diastereoisomers of 2,4-dimethoxy-5-(2,3-dideoxy-5-O-tritylribofuranosyl)pyrimidine. 2',3'-Dideoxy pyrimidine C-nucleosides by palladium-mediated glycal-aglycon coupling
  作者：Han Cheng Zhang、G. Doyle Daves

  DOI：10.1021/jo00061a034

  日期：1993.4

  Newly available enantiomeric 2,3-dideoxy glycals, (5S)- and (5R)-4,5-dihydro-5-[(triphenylmethoxy)-methyl] furans and 2,4-dimethoxy-5-iodopyrimidine undergo palladium-mediated coupling by two different, complementary procedures to form enantiomeric pairs of (2',3'-dideoxy-2',3'-didehydrofuranosyl)- and (2',3'-dideoxy-3',4'-didehydrofuranosyl)pyrimidine C-nucleosides. Stereoselective reductions of the carbohydrate unsaturations produce all four enantio- and diastereoisomers of 2,4-dimethoxy-5-(2,3-dideoxy-5-O-tritylribofuranosyl)pyrimidine. The facile two-step syntheses of 2',3'-deoxy C-nucleosides which involves preparation of a D-series C-nucleoside from an L-series glycal (and vice versa) represents a new strategy for C-nucleoside synthesis.