1-2',3',5'-tri-O-benzoyl-β-D-ribo-pentofuranosyl-4,6-diphenylpyrimidin-2-one | 1417444-56-4

• 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: 1-2',3',5'-tri-O-benzoyl-β-D-ribo-pentofuranosyl-4,6-diphenylpyrimidin-2-one
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(2-oxo-4,6-diphenylpyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 1417444-56-4
• 化学式: C₄₂H₃₂N₂O₈
• 分子量: 692.725
• InChiKey: HFZCVJMUFFZAOA-SIMZDOAPSA-N

物化性质

• 沸点：
  816.3±75.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  52
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  苯亚甲基苯乙酮 在 N,O-双三甲硅基乙酰胺 、 sodium ethanolate 、 甲烷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙腈 为溶剂， 反应 40.0h， 生成 1-2',3',5'-tri-O-benzoyl-β-D-ribo-pentofuranosyl-4,6-diphenylpyrimidin-2-one
  参考文献：
  名称：

  Synthesis of novel nucleosides and stereoselectivity of N-glycosidation

  摘要：

  An efficient synthetic route for novel nucleosides has been realized. We report the formation of alpha-isomers in spite of neighboring group participation by the benzoyl group at the 2-position in N-glycosidation as well as discuss the stereoselectivity observed. We also found that non-silylated pyrimidin-2(1H)-ones and pyrimidin-2(1H)-thiones having aromatic structures reacted with 1-fluororibose in the presence of a Lewis acid to give the corresponding nucleosides in good to high yield. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.017