<1S-<1α,2α,6α,8β,8aα>>-1,2,3,5,6,7,8,8a-octahydro-N,N,2-trimethyl-6-(phenylmethoxy)-8-<(trimethylsilyl)oxy>-1-naphthaleneacetamide | 143842-81-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: <1S-<1α,2α,6α,8β,8aα>>-1,2,3,5,6,7,8,8a-octahydro-N,N,2-trimethyl-6-(phenylmethoxy)-8-<(trimethylsilyl)oxy>-1-naphthaleneacetamide
• 英文别名: (1S-[1α,2α,6α,8β,8aα])-1,2,3,5,6,7,8,8a-octahydro-N,N,2-trimethyl-6-(phenylmethoxy)-8-[(trimethylsilyl)oxy]-1-naphthaleneacetamide；2-[(1S,2S,6R,8S,8aR)-2-methyl-6-phenylmethoxy-8-trimethylsilyloxy-1,2,3,5,6,7,8,8a-octahydronaphthalen-1-yl]-N,N-dimethylacetamide
• CAS: 143842-81-3
• 化学式: C₂₅H₃₉NO₃Si
• 分子量: 429.675
• InChiKey: FQWDYPVEBKUSCL-CXFMNZHWSA-N

物化性质

• 沸点：
  506.5±50.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <1S-<1α,2α,6α,8β,8aα>>-1,2,3,5,6,7,8,8a-octahydro-N,N,2-trimethyl-6-(phenylmethoxy)-8-<(trimethylsilyl)oxy>-1-naphthaleneacetamide 在 吡啶 、 4-二甲氨基吡啶 、 potassium tert-butylate 、 四丁基氟化铵 、 氨 、 水 、 lithium 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 27.25h， 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
• 作为产物：
  描述：

  2,2,2-三氯乙酰胺苄酯 在 三乙烯二胺 、 甲醇 、 氢氧化钾 、 草酰氯 、 三氟甲磺酸 、 dimethyl sulfide borane 、 potassium tert-butylate 、 双氧水 、 碘 、 二甲基氯化铝 、 二(3-甲基丁烷-2-基)硼烷 、 二异丁基氢化铝 、 二甲基亚砜 、 potassium iodide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 环己烷 为溶剂， 反应 54.3h， 生成 <1S-<1α,2α,6α,8β,8aα>>-1,2,3,5,6,7,8,8a-octahydro-N,N,2-trimethyl-6-(phenylmethoxy)-8-<(trimethylsilyl)oxy>-1-naphthaleneacetamide
  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.