(3aR,5S,6S,7S,7aR)-5-(methoxycarbonyl)-2-methyl-2-(((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)tetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl diacetate | 340016-47-9

• 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: (3aR,5S,6S,7S,7aR)-5-(methoxycarbonyl)-2-methyl-2-(((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)tetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl diacetate
• CAS: 340016-47-9
• 化学式: C₂₈H₄₀O₁₄
• 分子量: 600.617
• InChiKey: HPZJRCLVRQHKHE-HPAXYHHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  42.0
• 可旋转键数：
  5.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  152.74
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (3aR,5S,6S,7S,7aR)-5-(methoxycarbonyl)-2-methyl-2-(((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)tetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl diacetate 在 sodium carbonate 、 zinc(II) chloride 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成 β-glucuronide of α-dihydroartemisinin
  参考文献：
  名称：

  Efficient Preparations of the β-Glucuronides of Dihydroartemisinin and Structural Confirmation of the Human Glucuronide Metabolite

  摘要：

  New and greatly improved preparations of the 12 alpha ,1 ' beta- (5) and 12 beta ,1 ' beta- (6) glucuronides of dihydroartemisinin (DHA, 2) are reported using anomeric hydroxy and imidate glucuronate intermediates. Comparison of the synthetic and natural materials shows that the human metabolite of DHA is the 12 alpha -epimer 5.

  DOI：

  10.1021/jm001061a
• 作为产物：
  描述：

  dihydroartemisinin 、 3,4,6-三邻乙酰基-alpha-D-吡喃葡萄糖 1,2-(原酸甲酯) 在 zinc(II) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以78%的产率得到(3aR,5S,6S,7S,7aR)-5-(methoxycarbonyl)-2-methyl-2-(((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)tetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl diacetate
  参考文献：
  名称：

  Efficient Preparations of the β-Glucuronides of Dihydroartemisinin and Structural Confirmation of the Human Glucuronide Metabolite

  摘要：

  New and greatly improved preparations of the 12 alpha ,1 ' beta- (5) and 12 beta ,1 ' beta- (6) glucuronides of dihydroartemisinin (DHA, 2) are reported using anomeric hydroxy and imidate glucuronate intermediates. Comparison of the synthetic and natural materials shows that the human metabolite of DHA is the 12 alpha -epimer 5.

  DOI：

  10.1021/jm001061a