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 | 143857-19-6

• 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,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
• 英文别名: [(2R,4S,4aR,5S,6S)-4-acetyloxy-5-[2-[(2R,4R,6S)-4-hydroxy-6-methoxyoxan-2-yl]ethyl]-6-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-yl] acetate
• CAS: 143857-19-6
• 化学式: C₂₃H₃₆O₇
• 分子量: 424.535
• InChiKey: DTIVSEZLRNWJPV-HTHTXVELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 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,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 在 吡啶 、 咪唑 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 氢氧化钾 、 bis(acetylacetonate)oxovanadium 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 (S)-2-Methyl-butyric acid (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-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：

  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 双氧水 、 L-Selectride 作用下， 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

文献信息

• Remote diastereoselection in the asymmetric synthesis of pravastatin
  作者：A. R. Daniewski、P. M. Wovkulich、M. R. Uskokovic

  DOI：10.1021/jo00052a029

  日期：1992.12

  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.