20-(S),29-epoxylupan-3β-ol acetate | 65877-14-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 20-(S),29-epoxylupan-3β-ol acetate
• 英文别名: [(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-3a,5a,5b,8,8,11a-hexamethyl-1-[(2S)-2-methyloxiran-2-yl]-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] acetate
• CAS: 65877-14-7
• 化学式: C₃₂H₅₂O₃
• 分子量: 484.763
• InChiKey: PADBCQKCBWSBHV-KEHWVCINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  羽扇豆醇 在 吡啶 、 4-二甲氨基吡啶 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 51.0h， 生成 20-(S),29-epoxylupan-3β-ol acetate
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of Lupane and Olean-18-ene Derivatives. Absolute Configuration of 19,20-Epoxylupanes by VCD

  摘要：

  Lupane triterpenoids 2 and 5-12 and oleanene derivatives 13 and 14 were prepared from lupeol (1), betulin (3), and germanicol (4). They were tested for anti-HIV activity, and some structure-activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFT-calculated vibrational circular dichroism spectra. The CompareVOA algorithm was employed to support the C-20 configuration assignment. The 20,29 double bond in lupenone (2) and 3-epilupeol (15) was stereoselectively epoxidized to produce 20-(S)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structures.

  DOI：

  10.1021/np200910u

文献信息

• Synthesis and Anti-HIV Activity of Lupane and Olean-18-ene Derivatives. Absolute Configuration of 19,20-Epoxylupanes by VCD
  作者：Fátima Gutiérrez-Nicolás、Bárbara Gordillo-Román、Juan C. Oberti、Ana Estévez-Braun、Ángel G. Ravelo、Pedro Joseph-Nathan

  DOI：10.1021/np200910u

  日期：2012.4.27

  Lupane triterpenoids 2 and 5-12 and oleanene derivatives 13 and 14 were prepared from lupeol (1), betulin (3), and germanicol (4). They were tested for anti-HIV activity, and some structure-activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFT-calculated vibrational circular dichroism spectra. The CompareVOA algorithm was employed to support the C-20 configuration assignment. The 20,29 double bond in lupenone (2) and 3-epilupeol (15) was stereoselectively epoxidized to produce 20-(S)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structures.