(5R)-4,5-Dihydro-5-<(triphenylmethoxy)methyl>furan | 148440-97-5

• 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: (5R)-4,5-Dihydro-5-<(triphenylmethoxy)methyl>furan
• 英文别名: (2R)-2-(trityloxymethyl)-2,3-dihydrofuran
• CAS: 148440-97-5
• 化学式: C₂₄H₂₂O₂
• 分子量: 342.437
• InChiKey: FKHJWPHZBZUZRH-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5R)-4,5-Dihydro-5-<(triphenylmethoxy)methyl>furan 在 palladium on activated charcoal 、 palladium diacetate 四丁基氯化铵 、 氢气 、 sodium acetate 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、202.65 kPa 条件下， 反应 24.0h， 生成 2,4-dimethoxy-(2'R)-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：

  (R)-(-)-γ-三苯甲基甲氧基-γ-丁内酯 在 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 为溶剂， 反应 5.66h， 生成 (5R)-4,5-Dihydro-5-<(triphenylmethoxy)methyl>furan
  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