3,6-di-O-acetyl-5-(N''-benzyl-N'-phenylguanidino)-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose hydrochloride | 1010809-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3,6-di-O-acetyl-5-(N''-benzyl-N'-phenylguanidino)-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose hydrochloride
• 英文别名: [(2S)-2-[(3aR,5R,6S,6aR)-6-acetyloxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[(N'-benzyl-N-phenylcarbamimidoyl)amino]ethyl] acetate;hydrochloride
• CAS: 1010809-25-2
• 化学式: C₂₇H₃₃N₃O₇*ClH
• 分子量: 548.036
• InChiKey: CGCIGIXIVHYPLZ-DQGAKAOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,6-di-O-acetyl-5-(N''-benzyl-N'-phenylguanidino)-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose hydrochloride 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 5-(N''-benzyl-N'-phenylguanidino)-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose hydrochloride
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Guanidine-Type Iminosugars

  摘要：

  [GRAPHICS]The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported. The synthetic strategy involves the furanose -> piperidine rearrangement of 5-deoxy-5guanidino-L-idose precursors. The reaction proceeds through elimination of water to give 3-oxopiperidines, which were isolated as the corresponding hydrates. Biological evaluation of the new glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen atoms on the glycosidase inhibitory properties.

  DOI：

  10.1021/jo702374f
• 作为产物：
  描述：

  benzylamine hydrochloride 、 3,6-di-O-acetyl-5-deoxy-1,2-O-isopropylidene-5-(3-phenylcarbodiimido)-β-L-idofuranose 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以60%的产率得到3,6-di-O-acetyl-5-(N''-benzyl-N'-phenylguanidino)-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose hydrochloride
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Guanidine-Type Iminosugars

  摘要：

  [GRAPHICS]The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported. The synthetic strategy involves the furanose -> piperidine rearrangement of 5-deoxy-5guanidino-L-idose precursors. The reaction proceeds through elimination of water to give 3-oxopiperidines, which were isolated as the corresponding hydrates. Biological evaluation of the new glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen atoms on the glycosidase inhibitory properties.

  DOI：

  10.1021/jo702374f