methyl (1S,2S,4aR,6S,8S,8aS,3'R,2''S)-3'-(tert-butyldimethylsiloxy)-7'-<1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-<(2''-methylbutyryl)oxy>-1-naphthalenyl>-5'-oxohept-6'-enoate | 143633-63-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (1S,2S,4aR,6S,8S,8aS,3'R,2''S)-3'-(tert-butyldimethylsiloxy)-7'-<1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-<(2''-methylbutyryl)oxy>-1-naphthalenyl>-5'-oxohept-6'-enoate
• 英文别名: (1S,2S,4aR,6S,8S,8aS,5'R,2''S)-methyl-1,2,4a,5,6,7,8,8a-octahydro-5'-(tert-butyldimethylsilyloxy)-2,6-dimethyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthalenehept-1'-enoate；methyl (E,3R)-7-[(1S,2S,4aR,6S,8S,8aS)-2,6-dimethyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-[tert-butyl(dimethyl)silyl]oxy-5-oxohept-6-enoate
• CAS: 143633-63-0
• 化学式: C₃₁H₅₂O₆Si
• 分子量: 548.836
• InChiKey: VHOIJMZBFNJCMB-KOHTZEAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  38
• 可旋转键数：
  14
• 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：

  methyl (1S,2S,4aR,6S,8S,8aS,3'R,2''S)-3'-(tert-butyldimethylsiloxy)-7'-<1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-<(2''-methylbutyryl)oxy>-1-naphthalenyl>-5'-oxohept-6'-enoate 在 Wilkinson's catalyst 三乙基硅烷 、 sodium tetrahydroborate 、 氢氟酸 、 对甲苯磺酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 2.92h， 生成 (+)-Dihydromevinolin
  参考文献：
  名称：

  Total synthesis of (+)-dihydromevinolin

  摘要：

  DOI：

  10.1021/ja00275a053
• 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 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 N-[(2,4-二氯苯氧基)-甲氧基硫代膦酰]丙-2-胺 、 氢氟酸 、 sodium hexamethyldisilazane 、 三乙基硼氢化锂 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 134.83h， 生成 methyl (1S,2S,4aR,6S,8S,8aS,3'R,2''S)-3'-(tert-butyldimethylsiloxy)-7'-<1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-<(2''-methylbutyryl)oxy>-1-naphthalenyl>-5'-oxohept-6'-enoate
  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.
• Total synthesis of (+)-dihydromevinolin
  作者：Scott J. Hecker、Clayton H. Heathcock

  DOI：10.1021/ja00275a053

  日期：1986.7