N,N'-bis-(2,3,4-tri-O-acetyl-α-L-fucopyranosylmethyl)-tert-butylcarboxamide | 491851-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N'-bis-(2,3,4-tri-O-acetyl-α-L-fucopyranosylmethyl)-tert-butylcarboxamide
• 英文别名: [(2S,3R,4R,5R,6R)-4,5-diacetyloxy-2-methyl-6-[[(2-methylpropan-2-yl)oxycarbonyl-[[(2R,3R,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]methyl]amino]methyl]oxan-3-yl] acetate
• CAS: 491851-03-7
• 化学式: C₃₁H₄₇NO₁₆
• 分子量: 689.711
• InChiKey: WSBJZERLIMFIBV-SAOWUVMJSA-N

物化性质

• 沸点：
  657.0±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  206
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  N,N'-bis-(2,3,4-tri-O-acetyl-α-L-fucopyranosylmethyl)-tert-butylcarboxamide 在 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.08h， 生成 N,N'-bis-(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 12.0h， 生成 N,N'-bis-(2,3,4-tri-O-acetyl-α-L-fucopyranosylmethyl)-tert-butylcarboxamide
  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