(2S,3R,4S)-N'-benzyl-3,4,5,5-tetrahydroxy-2-(hydroxymethyl)-N-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]piperidine-1-carboximidamide;hydrochloride | 1010809-60-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S)-N'-benzyl-3,4,5,5-tetrahydroxy-2-(hydroxymethyl)-N-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]piperidine-1-carboximidamide;hydrochloride
• CAS: 1010809-60-5
• 化学式: C₂₁H₃₃N₃O₁₀*ClH
• 分子量: 523.968
• InChiKey: XWWPOJJDHFMDSP-FEOCVIKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.91
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  208
• 氢给体数：
  10
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-benzyl-1-[(1S)-2-hydroxy-1-[(2R,3R,4R)-3,4,5-trihydroxyoxolan-2-yl]ethyl]-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]guanidine;hydrochloride 在 Amberlite IRA 68 作用下， 以 水 为溶剂， 反应 0.5h， 以100%的产率得到(2S,3R,4S)-N'-benzyl-3,4,5,5-tetrahydroxy-2-(hydroxymethyl)-N-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]piperidine-1-carboximidamide;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  [GRAPHICS]The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported.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