(+)-ethyl (1S,2S,4aR,6S,8S,8aS)-6-(methoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2,2-dimethylbutyryl)oxy>naphthalene-1-carboxylate | 143633-58-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-ethyl (1S,2S,4aR,6S,8S,8aS)-6-(methoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2,2-dimethylbutyryl)oxy>naphthalene-1-carboxylate
• 英文别名: 1-O-ethyl 6-O-methyl (1S,2S,4aR,6S,8S,8aS)-8-(2,2-dimethylbutanoyloxy)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1,6-dicarboxylate
• CAS: 143633-58-3
• 化学式: C₂₂H₃₄O₆
• 分子量: 394.508
• InChiKey: FWUGAYIVLBIOOR-UGDFAFBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-ethyl (1S,2S,4aR,6S,8S,8aS)-6-(methoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2,2-dimethylbutyryl)oxy>naphthalene-1-carboxylate 在 重铬酸吡啶 、 3 A molecular sieve 、 三乙基硼氢化锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 ethyl (1S,2S,4aR,6S,8S,8aS)-8-(2,2-dimethylbutanoyloxy)-6-formyl-2-methyl-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
• 作为产物：
  描述：

  (+)-(1S,2S,4aR,6S,8S,8aS)-1-(ethoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6,8-naphthalenecarbolactone 在 吡啶 、 4-二甲氨基吡啶 、 sodium hexamethyldisilazane 作用下， 反应 18.0h， 生成 (+)-ethyl (1S,2S,4aR,6S,8S,8aS)-6-(methoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2,2-dimethylbutyryl)oxy>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

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.