1,2-dideoxy-2-fluoronojirimycin

• 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: 1,2-dideoxy-2-fluoronojirimycin
• 英文别名: 2-Fluoro-1,2,5-trideoxy-1,5-imino-D-glucitol；(2R,3R,4S,5S)-5-fluoro-2-(hydroxymethyl)piperidine-3,4-diol
• 化学式: C₆H₁₂FNO₃
• 分子量: 165.165
• InChiKey: KXZREBFWDJJIRA-SLPGGIOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  1-脱氧野尻霉素	1,5-dideoxy-1,5-imino-D-glucitol	19130-96-2	C6H13NO4	163.174

反应信息

• 作为产物：
  描述：

  1-脱氧野尻霉素 在 palladium on activated charcoal 氢气 、 sodium hydride 、 二正丁基氧化锡 、 碳酸氢钠 、 对甲苯磺酸 、 fluorhydrate de diisopropylamine 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 125.0 ℃ 、344.73 kPa 条件下， 反应 136.5h， 生成 1,2-dideoxy-2-fluoronojirimycin
  参考文献：
  名称：

  Khanna, Ish K.; Koszyk, Francis J.; Stealey, Michael A., Journal of Carbohydrate Chemistry, 1995, vol. 14, # 6, p. 843 - 878

  摘要：

  DOI：

文献信息

• Two isosteric fluorinated derivatives of the powerful glucosidase inhibitors, 1-deoxynojirimycin and 2,5-dideoxy-2,5-imino-d-mannitol: Syntheses and glucosidase-inhibitory activities of 1,2,5-trideoxy-2-fluoro-1,5-imino-d-glucitol and of 1,2,5-trideoxy-1-fluoro-2,5-imino-d-mannitol
  作者：Sören M. Andersen、Michael Ebner、Christian W. Ekhart、Günther Gradnig、Günter Legler、Inge Lundt、Arnold E. Stütz、Stephen G. Withers、Tanja Wrodnigg

  DOI：10.1016/s0008-6215(97)00099-2

  日期：1997.6

  1,2,5-Trideoxy-2-fluoro-1,5-imino-D-glucitol, the 2-deoxyfluoro derivative of 1-deoxynojirimycin, as well as 1,2,5-trideoxy-1-fluoro-2,5-imino-D-mannit and 2,5-dideoxy-2,5-imino-1-O-methyl-D-mannitol, two new analogues of the natural product and powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol, were synthesised featuring glucose isomerase-catalysed aldose-ketose interconversion reactions as the key steps of the syntheses. Results of inhibition studies conducted with these compounds and previously obtained deoxyfluoro derivatives of 1-deoxynojirimycin, employing glucosidases from various sources, showed that the replacement of a hydroxyl function by fluorine caused an impairment of the inhibitory potency. This effect was smallest for the hydroxyl group at C-6 and up to four orders of magnitude larger for replacements at C-2 and C-3. (C) 1997 Elsevier Science Ltd.
• Khanna, Ish K.; Koszyk, Francis J.; Stealey, Michael A., Journal of Carbohydrate Chemistry, 1995, vol. 14, # 6, p. 843 - 878
  作者：Khanna, Ish K.、Koszyk, Francis J.、Stealey, Michael A.、Weier, Richard M.、Julien, Janet、et al.

  DOI：——

  日期：——