N-(3,4-di-O-acetyl-α-L-fucopyranosylmethyl)-acetamide | 491850-99-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(3,4-di-O-acetyl-α-L-fucopyranosylmethyl)-acetamide
• 英文别名: [(2S,3R,4S,5R,6R)-6-(acetamidomethyl)-4-acetyloxy-5-hydroxy-2-methyloxan-3-yl] acetate
• CAS: 491850-99-8
• 化学式: C₁₃H₂₁NO₇
• 分子量: 303.312
• InChiKey: AFCMWLOPZIAOEB-DPKHYIIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 N-(3,4-di-O-acetyl-α-L-fucopyranosylmethyl)-acetamide 在 吡啶 、 1,4-bis(methylamino)pyridine 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以27%的产率得到N-(2,3,4-tri-O-acetyl-α-L-fucopyranosylmethyl)-acetamide
  参考文献：
  名称：

  Palladium−Charcoal-Catalyzed Reduction of Tri-O-acetyl-β-l-Fucopyranosyl Cyanide:  A Route to Small Cluster Oligosaccharide Mimetics (SCOMs)

  摘要：

  Synthesis of glycosyl cyanides was optimized with a new catalyst system. Reduction of tri-O-acetyl-beta-L-fucopyranosyl cyanide with Pd-hydrogen, in the presence of Ac2O and Boc(2)O, gave N-protected-mono- and -di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl)-amines, which allow for the syntheses of small cluster oligosaccharide mimetics of fucopyranosylomethyl-substituted ureas. From di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl) amine was also prepared a carbamoyl chloride as a potentially useful synthon for preparation of more complex C-glycosidic conjugates.

  DOI：

  10.1021/ol020123j
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-L-fucopyranose 在 palladium on activated charcoal 氢气 、 mercury dibromide 作用下， 以 硝基甲烷 、 乙酸乙酯 为溶剂， 20.0~70.0 ℃ 、8.27 MPa 条件下， 反应 84.0h， 生成 N-(3,4-di-O-acetyl-α-L-fucopyranosylmethyl)-acetamide
  参考文献：
  名称：

  Palladium−Charcoal-Catalyzed Reduction of Tri-O-acetyl-β-l-Fucopyranosyl Cyanide:  A Route to Small Cluster Oligosaccharide Mimetics (SCOMs)

  摘要：

  Synthesis of glycosyl cyanides was optimized with a new catalyst system. Reduction of tri-O-acetyl-beta-L-fucopyranosyl cyanide with Pd-hydrogen, in the presence of Ac2O and Boc(2)O, gave N-protected-mono- and -di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl)-amines, which allow for the syntheses of small cluster oligosaccharide mimetics of fucopyranosylomethyl-substituted ureas. From di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl) amine was also prepared a carbamoyl chloride as a potentially useful synthon for preparation of more complex C-glycosidic conjugates.

  DOI：

  10.1021/ol020123j