(4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-((1S,2S,6R,8S,8aR)-8-dimethylsilanyloxy-2,6-dimethyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-tetrahydro-pyran-2-one | 134004-73-2

• 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: (4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-((1S,2S,6R,8S,8aR)-8-dimethylsilanyloxy-2,6-dimethyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-tetrahydro-pyran-2-one
• CAS: 134004-73-2
• 化学式: C₂₇H₅₀O₄Si₂
• 分子量: 494.863
• InChiKey: OPWMQQXPQXUXSJ-MDENKYSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.86
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-((1S,2S,6R,8S,8aR)-8-dimethylsilanyloxy-2,6-dimethyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-tetrahydro-pyran-2-one 在 dihydrogen hexachloroplatinate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Novel synthesis of mevinolin-related compounds. Large-scale preparation of HMG-CoA reductase inhibitor L-679,336

  摘要：

  A novel synthetic route to a mevinolin-related HMG-CoA reductase inhibitor L-679,336 is described. The key features of the synthesis are a diastereoselective osmium tetraoxide catalyzed dihydroxylation reaction and a highly selective, phosphorus-mediated, pinacol-type rearrangement to give ketone 6. In situ multinuclear NMR experiments were used to gain a detailed understanding of the pinacol step. The above route was used for multikilogram preparation of the title compound. Also described are Lewis acid catalyzed rearrangement reactions of epoxide intermediates 4 and 5, as well as the intramolecular hydrosilylation reaction of deacylated olefinic substrates 17 and 18.

  DOI：

  10.1021/jo00011a022
• 作为产物：
  描述：

  莫那可林J 在 Wilkinson's catalyst 咪唑 、 氢气 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 40.0 ℃ 、275.79 kPa 条件下， 生成 (4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-((1S,2S,6R,8S,8aR)-8-dimethylsilanyloxy-2,6-dimethyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Novel synthesis of mevinolin-related compounds. Large-scale preparation of HMG-CoA reductase inhibitor L-679,336

  摘要：

  A novel synthetic route to a mevinolin-related HMG-CoA reductase inhibitor L-679,336 is described. The key features of the synthesis are a diastereoselective osmium tetraoxide catalyzed dihydroxylation reaction and a highly selective, phosphorus-mediated, pinacol-type rearrangement to give ketone 6. In situ multinuclear NMR experiments were used to gain a detailed understanding of the pinacol step. The above route was used for multikilogram preparation of the title compound. Also described are Lewis acid catalyzed rearrangement reactions of epoxide intermediates 4 and 5, as well as the intramolecular hydrosilylation reaction of deacylated olefinic substrates 17 and 18.

  DOI：

  10.1021/jo00011a022