(4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-((1S,2S)-2,6-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethyl]-tetrahydro-pyran-2-one | 134004-71-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-((1S,2S)-2,6-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethyl]-tetrahydro-pyran-2-one
• CAS: 134004-71-0
• 化学式: C₂₅H₄₀O₃Si
• 分子量: 416.676
• InChiKey: CAWZDZUPGLRIJF-PDGJWGCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  6(R)-<2<<1a(R),8a(S)>-4(S)-<(2,2-dimethylbutyryl)oxy>-2(R),6(S)-dimethyl-1a,2,4,4a,5,6,7,8-octahydro-3H-naphth<1,8a-b>oxiran-5-yl>ethyl>-4(R)-(tert-butyldimethylsiloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one 在 三氟甲磺酸三甲基硅酯 、 lutidine 作用下， 生成 (4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-((1S,2S)-2,6-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethyl]-tetrahydro-pyran-2-one 、 2,2-Dimethyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl ester 、 2,2-Dimethyl-butyric acid (1S,3R,4R,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-hydroxy-3,7-dimethyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
  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