(S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester | 143842-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
• 英文别名: [(1S,3S,7S,8S,8aR)-3-[tert-butyl(diphenyl)silyl]oxy-8-[2-[(2R,4R)-4-[tert-butyl(diphenyl)silyl]oxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
• CAS: 143842-95-9
• 化学式: C₅₅H₇₀O₆Si₂
• 分子量: 883.328
• InChiKey: ZGZUXGOMSQLSHE-IIZRFTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.09
• 重原子数：
  63
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 29.0h， 以85%的产率得到普伐他汀类酯
  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 吡啶 、 咪唑 、 2,6-二甲基吡啶 、 chromium(VI) oxide 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 氢氧化钾 、 methoxycarbonylsulfamoyl-triethylammmonium hydroxide 、 bis(acetylacetonate)oxovanadium 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 双氧水 、 L-Selectride 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 61.25h， 生成 (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-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.