Acetic acid (1S,3R,7S,8S,8aR)-3-acetoxy-8-[2-((2R,6S)-6-methoxy-4-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester | 143842-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: Acetic acid (1S,3R,7S,8S,8aR)-3-acetoxy-8-[2-((2R,6S)-6-methoxy-4-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
• 英文别名: [(2R,4S,4aR,5S,6S)-4-acetyloxy-5-[2-[(2R,6S)-6-methoxy-4-oxooxan-2-yl]ethyl]-6-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-yl] acetate
• CAS: 143842-90-4
• 化学式: C₂₃H₃₄O₇
• 分子量: 422.519
• InChiKey: GEWXGRCPKJLNGM-HMFGLBQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,3R,7S,8S,8aR)-3-acetoxy-8-[2-((2R,6S)-6-methoxy-4-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester 在 咪唑 、 氢氧化钾 、 双氧水 、 L-Selectride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 (1S,3R,7S,8S,8aR)-3-(tert-Butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-ol
  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 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 22.0h， 生成 Acetic acid (1S,3R,7S,8S,8aR)-3-acetoxy-8-[2-((2R,6S)-6-methoxy-4-oxo-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