Ethyl (1S,2S,4aR,6S,8S,8aS) 8-(tert-Butyldimethylsilyloxy)-6-formyl-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate | 143435-64-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: Ethyl (1S,2S,4aR,6S,8S,8aS) 8-(tert-Butyldimethylsilyloxy)-6-formyl-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate
• 英文别名: ethyl (1S,2S,4aR,6S,8S,8aS)-8-[tert-butyl(dimethyl)silyl]oxy-6-formyl-2,6-dimethyl-2,4a,5,7,8,8a-hexahydro-1H-naphthalene-1-carboxylate
• CAS: 143435-64-7
• 化学式: C₂₂H₃₈O₄Si
• 分子量: 394.627
• InChiKey: MIUJHQVQLIUWBM-CCHWJJJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-二碘乙烷 、 Ethyl (1S,2S,4aR,6S,8S,8aS) 8-(tert-Butyldimethylsilyloxy)-6-formyl-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate 在 chromium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 ethyl (1S,2S,4aR,6S,8S,8aS)-8-[tert-butyl(dimethyl)silyl]oxy-2,6-dimethyl-6-[(E)-prop-1-enyl]-2,4a,5,7,8,8a-hexahydro-1H-naphthalene-1-carboxylate
  参考文献：
  名称：

  Total synthesis of dihydromevinolin and a series of related 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors

  摘要：

  The natural product dihydromevinolin, 2, and a series of structurally related 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, 3-6, have been synthesized. The key features are an intramolecular Diels-Alder reaction to form a functionalized decalin skeleton with six asymmetric centers in a stereocontrolled manner, the selective manipulation of the functional groups, and an improved method for the introduction and elaboration of the delta-lactone portion. Analogue 6 was approximately 10-fold more potent than 2 as an inhibitor and was produced in multigram quantities.

  DOI：

  10.1021/jo00047a011
• 作为产物：
  描述：

  (1S,2S,3S,4S,7R,9S)-4,9-Dimethyl-10-oxo-11-oxa-tricyclo[7.2.1.0^2,7]dodec-5-ene-3-carboxylic acid ethyl ester 在 2,6-二甲基吡啶 、 草酰氯 、 sodium hexamethyldisilazane 、 三乙基硼氢化锂 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 Ethyl (1S,2S,4aR,6S,8S,8aS) 8-(tert-Butyldimethylsilyloxy)-6-formyl-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Total synthesis of dihydromevinolin and a series of related 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors

  摘要：

  The natural product dihydromevinolin, 2, and a series of structurally related 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, 3-6, have been synthesized. The key features are an intramolecular Diels-Alder reaction to form a functionalized decalin skeleton with six asymmetric centers in a stereocontrolled manner, the selective manipulation of the functional groups, and an improved method for the introduction and elaboration of the delta-lactone portion. Analogue 6 was approximately 10-fold more potent than 2 as an inhibitor and was produced in multigram quantities.

  DOI：

  10.1021/jo00047a011

文献信息

• Total synthesis of dihydromevinolin and a series of related 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors
  作者：Christopher M. Blackwell、Alan H. Davidson、Steven B. Launchbury、Christopher N. Lewis、Elizabeth M. Morrice、Maxwell M. Reeve、Jonathon A. R. Roffey、Andrew S. Tipping、Richard S. Todd

  DOI：10.1021/jo00047a011

  日期：1992.10

  The natural product dihydromevinolin, 2, and a series of structurally related 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, 3-6, have been synthesized. The key features are an intramolecular Diels-Alder reaction to form a functionalized decalin skeleton with six asymmetric centers in a stereocontrolled manner, the selective manipulation of the functional groups, and an improved method for the introduction and elaboration of the delta-lactone portion. Analogue 6 was approximately 10-fold more potent than 2 as an inhibitor and was produced in multigram quantities.