(3S,4R,5S)-3,4,5-tris(benzyloxy)piperidin-2-one | 1152509-08-4

• 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)piperidin-2-one
• 英文别名: (3S,4R,5S)-3,4,5-tris(phenylmethoxy)piperidin-2-one
• CAS: 1152509-08-4
• 化学式: C₂₆H₂₇NO₄
• 分子量: 417.505
• InChiKey: YBVMEGYOLUGZQE-GVAUOCQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-3,4,5-tris(benzyloxy)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-trihydroxypiperidin-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：

  (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-one 在 氨 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以80%的产率得到(3S,4R,5S)-3,4,5-tris(benzyloxy)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

• Synthesis and in vitro anti-hepatitis B virus activity of six-membered azanucleoside analogues
  作者：Dan Wang、Yu-Huan Li、Yu-Ping Wang、Rong-Mei Gao、Li-He Zhang、Xin-Shan Ye

  DOI：10.1016/j.bmc.2010.11.063

  日期：2011.1

  Fifteen novel six-membered azanucleoside derivatives were prepared and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in human hepatoblastoma-derived liver Hep-G2 cells. The most potent compound 16b with an IC50 value of 2.74 μg/mL (lower than 3TC) and a SI value of 13.5 was disclosed. The key synthetic steps involved the rearrangement of lactones (which were readily obtained

  制备了十五种新颖的六元氮杂核苷衍生物，并对其在人肝母细胞瘤衍生的肝Hep-G2细胞中的抗乙型肝炎病毒（HBV）活性和细胞毒性进行了评估。最强效的化合物16b，IC 50公开了2.74μg/ mL的值（低于3TC）和13.5的SI值。关键的合成步骤涉及内酯的重排（很容易从单糖中获得）和路易斯酸催化的碱基与氮杂糖供体的缩合。使用通用的乙酰化氮杂糖供体，成功获得了覆盖三种类型的氮杂糖和四种类型的天然核碱基的氮杂核苷。实验结果表明，某些六元氮杂核苷可能会在发现新的抗病毒药物中找到应用。