(2S,3S,4S,5S)-2-butylpiperidine-3,4,5-triol | 1309459-14-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (2S,3S,4S,5S)-2-butylpiperidine-3,4,5-triol
• CAS: 1309459-14-0
• 化学式: C₉H₁₉NO₃
• 分子量: 189.255
• InChiKey: ZWDYCEWSIGKXOD-JBDRJPRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 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：
  4

反应信息

• 作为产物：
  描述：

  D-(-)-古洛糖酸-gamma-内酯 在 盐酸 、 甲醇 、 硫酸 、 SiO₂-supported NaIO₄ 、 水 、 四丁基碘化铵 、 二异丁基氢化铝 、 copper(II) sulfate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (2S,3S,4S,5S)-2-butylpiperidine-3,4,5-triol
  参考文献：
  名称：

  1-C-Alkyl imino-d-xylitol and -l-arabinitol derivatives obtained via nucleophilic addition to pentose-derived N-tert-butanesulfinyl imines: sugar- versus chiral auxiliary-induced stereoselectivity

  摘要：

  The stereoselective synthesis of 1-C-alkyl iminosugars in the D-xylo and L-arabino series as potential drugs for the treatment of lysosomal diseases has been achieved. The key step involves nucleophilic addition to pentodialdofuranose-derived imines generated using enantiopure tert-butanesulfinamide. Depending on the pentofuranose configuration and structure, the stereoselectivity of this reaction was found to be controlled either by the sugar moiety or by the stereogenic sulfur center. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.024

文献信息

• 1-C-Alkyl imino-d-xylitol and -l-arabinitol derivatives obtained via nucleophilic addition to pentose-derived N-tert-butanesulfinyl imines: sugar- versus chiral auxiliary-induced stereoselectivity
  作者：Farah Oulaïdi、Estelle Gallienne、Philippe Compain、Olivier R. Martin

  DOI：10.1016/j.tetasy.2011.02.024

  日期：2011.3

  The stereoselective synthesis of 1-C-alkyl iminosugars in the D-xylo and L-arabino series as potential drugs for the treatment of lysosomal diseases has been achieved. The key step involves nucleophilic addition to pentodialdofuranose-derived imines generated using enantiopure tert-butanesulfinamide. Depending on the pentofuranose configuration and structure, the stereoselectivity of this reaction was found to be controlled either by the sugar moiety or by the stereogenic sulfur center. (C) 2011 Elsevier Ltd. All rights reserved.