Acetic acid (1S,3R,7S,8S,8aR)-3-acetoxy-7-methyl-8-[2-((R)-4-oxo-3,4-dihydro-2H-pyran-2-yl)-ethyl]-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester | 143842-88-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (1S,3R,7S,8S,8aR)-3-acetoxy-7-methyl-8-[2-((R)-4-oxo-3,4-dihydro-2H-pyran-2-yl)-ethyl]-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
• 英文别名: [(2R,4S,4aR,5S,6S)-4-acetyloxy-6-methyl-5-[2-[(2R)-4-oxo-2,3-dihydropyran-2-yl]ethyl]-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-yl] acetate
• CAS: 143842-88-0
• 化学式: C₂₂H₃₀O₆
• 分子量: 390.477
• InChiKey: FLUMXJHSJNTVCJ-IUQPLPALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,3R,7S,8S,8aR)-3-acetoxy-7-methyl-8-[2-((R)-4-oxo-3,4-dihydro-2H-pyran-2-yl)-ethyl]-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester 在 双氧水 、 L-Selectride 、 三乙胺 作用下， 反应 20.5h， 生成 Acetic acid (1S,3R,7S,8S,8aR)-3-acetoxy-8-[2-((2R,4R,6S)-4-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
  参考文献：
  名称：

  Remote diastereoselection in the asymmetric synthesis of pravastatin

  摘要：

  The first total synthesis of pravastatin (3) is described. The desymmetrization of 1-methyl-4-methylenecyclohexane (10) by an asymmetric ene reaction to form 11a provided the initial asymmetric framework. The remaining stereogenic centers were introduced sequentially by a series of diastereoselective processes which include the iodolactonization of 11a to 13. the Eschenmoser-Claisen rearrangement of 17 to 18, the stereoselective intramolecular ene reaction of 20 to 21. and the diastereoselective condensation of aldehyde 27 with diene 28.

  DOI：

  10.1021/jo00052a029
• 作为产物：
  描述：

  (1S,3R,7S,8S,8aR)-8-((E)-3-Methoxy-allyl)-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalene-1,3-diol 在 吡啶 、 4-二甲氨基吡啶 、 水 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 Acetic acid (1S,3R,7S,8S,8aR)-3-acetoxy-7-methyl-8-[2-((R)-4-oxo-3,4-dihydro-2H-pyran-2-yl)-ethyl]-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
  参考文献：
  名称：

  Remote diastereoselection in the asymmetric synthesis of pravastatin

  摘要：

  The first total synthesis of pravastatin (3) is described. The desymmetrization of 1-methyl-4-methylenecyclohexane (10) by an asymmetric ene reaction to form 11a provided the initial asymmetric framework. The remaining stereogenic centers were introduced sequentially by a series of diastereoselective processes which include the iodolactonization of 11a to 13. the Eschenmoser-Claisen rearrangement of 17 to 18, the stereoselective intramolecular ene reaction of 20 to 21. and the diastereoselective condensation of aldehyde 27 with diene 28.

  DOI：

  10.1021/jo00052a029