5-(2,4:3,5-di-O-benzylidene-D-pentitol-1-yl)nicotinamide | 107325-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(2,4:3,5-di-O-benzylidene-D-pentitol-1-yl)nicotinamide
• CAS: 107325-64-4；107325-65-5；139345-49-6
• 化学式: C₂₅H₂₄N₂O₆
• 分子量: 448.475
• InChiKey: HFYUBPBLDFWUHS-PWNUNKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  113.13
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-(2,4:3,5-di-O-benzylidene-D-pentitol-1-yl)nicotinamide 在 4-二甲氨基吡啶 、 氯甲烷 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 5-[(2S,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]吡啶-3-甲酰胺
  参考文献：
  名称：

  Nucleosides. 141. Synthesis of 5-.beta.-D-ribofuranosylnicotinamide and its N-methyl derivative. The isosteric and isoelectronic analogs of nicotinamide nucleoside

  摘要：

  The pyridine C-nucleosides 5-beta-D-ribofuranosylnicotinamide and its N-methylpyridinium derivative (1 and 2), which are isosteric and isoelectronic, respectively, to nicotinamide nucleoside were synthesized. Condensation of 3-bromo-5-lithiopyridine with 2,4:3,5-di-O-benzylidene-D-aldehydoribose (7) afforded an allo/altro mixture of the corresponding bromopyridine derivatives, which were converted into nicotinamide C-nucleoside precursors 10. Mesylation of the hydroxyl group of 10 followed by acid hydrolysis of the product afforded the anomeric nicotinamide C-nucleosides. The beta anomer 1 was separated and treated with MeI to give 2.

  DOI：

  10.1021/jm00388a030
• 作为产物：
  描述：

  methyl 5-(2,4:3,5-di-O-benzylidene-D-pentitol-1-yl)nicotinate 在 氨 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以87%的产率得到5-(2,4:3,5-di-O-benzylidene-D-pentitol-1-yl)nicotinamide
  参考文献：
  名称：

  Nucleosides. 141. Synthesis of 5-.beta.-D-ribofuranosylnicotinamide and its N-methyl derivative. The isosteric and isoelectronic analogs of nicotinamide nucleoside

  摘要：

  The pyridine C-nucleosides 5-beta-D-ribofuranosylnicotinamide and its N-methylpyridinium derivative (1 and 2), which are isosteric and isoelectronic, respectively, to nicotinamide nucleoside were synthesized. Condensation of 3-bromo-5-lithiopyridine with 2,4:3,5-di-O-benzylidene-D-aldehydoribose (7) afforded an allo/altro mixture of the corresponding bromopyridine derivatives, which were converted into nicotinamide C-nucleoside precursors 10. Mesylation of the hydroxyl group of 10 followed by acid hydrolysis of the product afforded the anomeric nicotinamide C-nucleosides. The beta anomer 1 was separated and treated with MeI to give 2.

  DOI：

  10.1021/jm00388a030