(2S,3R,4S)-1-(N'-benzyl-N-phenylamidino)-3,4,5,5-tetrahydroxy-2-hydroxymethylpiperidine hydrochloride | 1010809-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (2S,3R,4S)-1-(N'-benzyl-N-phenylamidino)-3,4,5,5-tetrahydroxy-2-hydroxymethylpiperidine hydrochloride
• 英文别名: (2S,3R,4S)-N'-benzyl-3,4,5,5-tetrahydroxy-2-(hydroxymethyl)-N-phenylpiperidine-1-carboximidamide;hydrochloride
• CAS: 1010809-55-8
• 化学式: C₂₀H₂₅N₃O₅*ClH
• 分子量: 423.897
• InChiKey: CDNSZSYKUREZED-RXQQAGQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.16
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  129
• 氢给体数：
  7
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-(N''-benzyl-N'-phenylguanidino)-5-deoxy-L-idofuranose 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)-1-(N'-benzyl-N-phenylamidino)-3,4,5,5-tetrahydroxy-2-hydroxymethylpiperidine 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  [GRAPHICS]The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported.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