methyl 5-(2,4:3,5-di-O-benzylidene-1-O-mesyl-D-pentitol-1-yl)nicotinamide | 107325-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: methyl 5-(2,4:3,5-di-O-benzylidene-1-O-mesyl-D-pentitol-1-yl)nicotinamide
• CAS: 107325-66-6；107436-61-3；139345-50-9
• 化学式: C₂₆H₂₆N₂O₈S
• 分子量: 526.567
• InChiKey: VWHWSLHBIXMMKJ-WGZTVAFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  136.27
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 5-(2,4:3,5-di-O-benzylidene-1-O-mesyl-D-pentitol-1-yl)nicotinamide 在 氯甲烷 、 三氟乙酸 作用下， 反应 0.25h， 生成 5-(α-D-ribofuranosyl)nicotinamide 、 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 4-二甲氨基吡啶 、 氨 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 methyl 5-(2,4:3,5-di-O-benzylidene-1-O-mesyl-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