6-((2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-piperidin-1-yl)-hexanenitrile | 885484-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 6-((2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-piperidin-1-yl)-hexanenitrile
• CAS: 885484-36-6
• 化学式: C₁₂H₂₂N₂O₄
• 分子量: 258.318
• InChiKey: HXEZRPYPLRABDR-NOOOWODRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.17
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  107.95
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-((2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-piperidin-1-yl)-hexanenitrile 在 镍 氢气 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5-(dimethylamino)-N-(6-((2R,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl)hexyl)naphthalene-1-sulfonamide
  参考文献：
  名称：

  Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols

  摘要：

  1,5-Dideoxy-1,5-iminoalditols of various configurations as well as isofagomine were N-alkylated with non-polar straight chain spacer-arms by a set of simple standard procedures. The spacer-arms' terminal functional groups, primary amines, were employed to introduce fluorescent tags such as dansyl and dapoxyl moieties. Resulting derivatives in the D-xylo, D-gluco, D-galacto as well as GlcNAc series showed distinctly improved glycosidase inhibitory activities compared to parent compounds and are designed to be useful analytical tools. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.095
• 作为产物：
  描述：

  6-溴己腈 、 米加司他 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 6-((2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-piperidin-1-yl)-hexanenitrile
  参考文献：
  名称：

  Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols

  摘要：

  1,5-Dideoxy-1,5-iminoalditols of various configurations as well as isofagomine were N-alkylated with non-polar straight chain spacer-arms by a set of simple standard procedures. The spacer-arms' terminal functional groups, primary amines, were employed to introduce fluorescent tags such as dansyl and dapoxyl moieties. Resulting derivatives in the D-xylo, D-gluco, D-galacto as well as GlcNAc series showed distinctly improved glycosidase inhibitory activities compared to parent compounds and are designed to be useful analytical tools. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.095