(3S,4R,5S)-3,4,5-tris(benzyloxy)-1-(6-hydroxyhexyl)piperidin-2-one | 1152509-01-7

• 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-(6-hydroxyhexyl)piperidin-2-one
• 英文别名: (3S,4R,5S)-1-(6-hydroxyhexyl)-3,4,5-tris(phenylmethoxy)piperidin-2-one
• CAS: 1152509-01-7
• 化学式: C₃₂H₃₉NO₅
• 分子量: 517.665
• InChiKey: YYPNDFGMDGNFPB-YPKYBTACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-3,4,5-tris(benzyloxy)-1-(6-hydroxyhexyl)piperidin-2-one 在 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 24.0h， 以99%的产率得到(3S,4R,5S)-3,4,5-trihydroxy-1-(6-hydroxyhexyl)piperidin-2-one
  参考文献：
  名称：

  Rational Design and Synthesis of Highly Potent Pharmacological Chaperones for Treatment of N370S Mutant Gaucher Disease

  摘要：

  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).

  DOI：

  10.1021/jm801506m
• 作为产物：
  描述：

  6-氨基-1-己醇 、 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-one 在 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以62%的产率得到(3S,4R,5S)-3,4,5-tris(benzyloxy)-1-(6-hydroxyhexyl)piperidin-2-one
  参考文献：
  名称：

  Rational Design and Synthesis of Highly Potent Pharmacological Chaperones for Treatment of N370S Mutant Gaucher Disease

  摘要：

  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).

  DOI：

  10.1021/jm801506m

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).