N-(2-hydroxyethyl)-1,6-dideoxynojirimycin | 936567-44-1

• 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: N-(2-hydroxyethyl)-1,6-dideoxynojirimycin
• 英文别名: (2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-methylpiperidine-3,4,5-triol
• CAS: 936567-44-1
• 化学式: C₈H₁₇NO₄
• 分子量: 191.227
• InChiKey: RHSXPHNUNZVEGD-ULAWRXDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-N-(2-hydroxyethyl)-1,6-dideoxynojirimycin 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以92%的产率得到N-(2-hydroxyethyl)-1,6-dideoxynojirimycin
  参考文献：
  名称：

  An expeditious one-pot synthesis of 1,6-dideoxy-N-alkylated nojirimycin derivatives and their inhibitory effects on the secretion of IFN-γ and IL-4

  摘要：

  An efficient 'one-pot' approach to the synthesis of 1,6-dideoxy-N-alkylated nojirimycin derivatives in good yields and with high stereoselectivity was developed. It was found that the synthetic N-alkylated iminosugars showed inhibitory effects on the release of the cytokines IFN-gamma and IL-4 from the mouse splenocytes. The preliminary structure-activity relationship was deduced from the activities of N-substituted iminosugars. Apart from the cytokine inhibitory activities, a series of glycosidase inhibitory activities were also examined. The present experimental data demonstrated that synthetic iminosugars might hold potential as immunosuppressive agents. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.036

文献信息

• An expeditious one-pot synthesis of 1,6-dideoxy-N-alkylated nojirimycin derivatives and their inhibitory effects on the secretion of IFN-γ and IL-4
  作者：Jian Zhou、Yongmin Zhang、Xia Zhou、Jing Zhou、Li-He Zhang、Xin-Shan Ye、Xiao-Lian Zhang

  DOI：10.1016/j.bmc.2007.11.036

  日期：2008.2.15

  An efficient 'one-pot' approach to the synthesis of 1,6-dideoxy-N-alkylated nojirimycin derivatives in good yields and with high stereoselectivity was developed. It was found that the synthetic N-alkylated iminosugars showed inhibitory effects on the release of the cytokines IFN-gamma and IL-4 from the mouse splenocytes. The preliminary structure-activity relationship was deduced from the activities of N-substituted iminosugars. Apart from the cytokine inhibitory activities, a series of glycosidase inhibitory activities were also examined. The present experimental data demonstrated that synthetic iminosugars might hold potential as immunosuppressive agents. (C) 2007 Elsevier Ltd. All rights reserved.