(3S,4R,5S)-3,4,5-tris(benzyloxy)-1-octylpiperidin-2-one | 1152508-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4R,5S)-3,4,5-tris(benzyloxy)-1-octylpiperidin-2-one
• 英文别名: (3S,4R,5S)-1-octyl-3,4,5-tris(phenylmethoxy)piperidin-2-one
• CAS: 1152508-92-3
• 化学式: C₃₄H₄₃NO₄
• 分子量: 529.72
• InChiKey: PKEPVSGBUUQDOM-DSPMFFIESA-N

物化性质

• 沸点：
  651.7±55.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-3,4,5-tris(benzyloxy)-1-octylpiperidin-2-one 在 硼烷四氢呋喃络合物 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 28.3h， 生成 (3R,4r,5S)-1-octylpiperidine-3,4,5-triol
  参考文献：
  名称：

  Synthetic N-Alkylated Iminosugars as New Potential Immunosuppressive Agents

  摘要：

  The new emerging immunosuppressive effects displayed by iminosugars have not been much investigated so far. Several new N-alkyl dideoxy iminoalditols were designed and synthesized to explore their immunosuppressive effects. These iminosugars inhibited the proliferation of mouse splenocytes and the secretion of both IFN-gamma and IL-4, which are the hallmark cytokines of Th1 and Th2 cells, respectively. Some compounds exerted good inhibitory effects. More importantly, the synthetic iminosugars prolonged the allograft survival in the mouse skin transplantation experiment. Our results provide a lead for further elucidation of the structure-activity relationships and modifications of iminosugars for better immunosuppressive agents.

  DOI：

  10.1021/ml2000998
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 在 sodium cyanoborohydride 、 臭氧 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 生成 (3S,4R,5S)-3,4,5-tris(benzyloxy)-1-octylpiperidin-2-one
  参考文献：
  名称：

  Synthetic N-Alkylated Iminosugars as New Potential Immunosuppressive Agents

  摘要：

  The new emerging immunosuppressive effects displayed by iminosugars have not been much investigated so far. Several new N-alkyl dideoxy iminoalditols were designed and synthesized to explore their immunosuppressive effects. These iminosugars inhibited the proliferation of mouse splenocytes and the secretion of both IFN-gamma and IL-4, which are the hallmark cytokines of Th1 and Th2 cells, respectively. Some compounds exerted good inhibitory effects. More importantly, the synthetic iminosugars prolonged the allograft survival in the mouse skin transplantation experiment. Our results provide a lead for further elucidation of the structure-activity relationships and modifications of iminosugars for better immunosuppressive agents.

  DOI：

  10.1021/ml2000998

文献信息

• Rational Design and Synthesis of Highly Potent Pharmacological Chaperones for Treatment of N370S Mutant Gaucher Disease
  作者：Guan-Nan Wang、Gabriele Reinkensmeier、Si-Wei Zhang、Jian Zhou、Liang-Ren Zhang、Li-He Zhang、Terry D. Butters、Xin-Shan Ye

  DOI：10.1021/jm801506m

  日期：2009.5.28

  Highly potent N-substituted delta-lactams have been rationally designed and synthesized by a concise route with a one-pot tandem reaction as key step. These iminosugars show weak inhibition of wildtype beta-glucocerebrosidase but 3- to 6-fold increases in mutant enzyme activity (N370S).
• Synthetic N-Alkylated Iminosugars as New Potential Immunosuppressive Agents
  作者：Guan-Nan Wang、Yulan Xiong、Jia Ye、Li-He Zhang、Xin-Shan Ye

  DOI：10.1021/ml2000998

  日期：2011.9.8

  The new emerging immunosuppressive effects displayed by iminosugars have not been much investigated so far. Several new N-alkyl dideoxy iminoalditols were designed and synthesized to explore their immunosuppressive effects. These iminosugars inhibited the proliferation of mouse splenocytes and the secretion of both IFN-gamma and IL-4, which are the hallmark cytokines of Th1 and Th2 cells, respectively. Some compounds exerted good inhibitory effects. More importantly, the synthetic iminosugars prolonged the allograft survival in the mouse skin transplantation experiment. Our results provide a lead for further elucidation of the structure-activity relationships and modifications of iminosugars for better immunosuppressive agents.