methyl (1S,2S,4aR,6S,8S,8aS,3'R)-7-<1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2'',2''-dimethyl-1''-oxobutyl)oxy>-6-<(E)-prop-1-enyl>-1-naphthalenyl>-3'-<(tert-butyldimethylsilyl)oxy>-5'-oxohept-6'-enoate | 139040-00-9

• 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)-7-<1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2'',2''-dimethyl-1''-oxobutyl)oxy>-6-<(E)-prop-1-enyl>-1-naphthalenyl>-3'-<(tert-butyldimethylsilyl)oxy>-5'-oxohept-6'-enoate
• 英文别名: methyl (1S,2S,4aR,6S,8S,8aS,3'R)-3'-(tert-butyldimethylsiloxy)-7'-<1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2'',2''-dimethylbutyryl)oxy>-6-<(E)-prop-1-enyl>-1-naphthalenyl>-5'-oxohept-6'-enoate；methyl (E,3R)-7-[(1S,2S,4aR,6S,8S,8aS)-8-(2,2-dimethylbutanoyloxy)-2-methyl-6-[(E)-prop-1-enyl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-[tert-butyl(dimethyl)silyl]oxy-5-oxohept-6-enoate
• CAS: 139040-00-9
• 化学式: C₃₄H₅₆O₆Si
• 分子量: 588.901
• InChiKey: MNLHITSAQWYPHT-GGQHCSTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 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)-7-<1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2'',2''-dimethyl-1''-oxobutyl)oxy>-6-<(E)-prop-1-enyl>-1-naphthalenyl>-3'-<(tert-butyldimethylsilyl)oxy>-5'-oxohept-6'-enoate 在 碲化氢 、 sodium tetrahydroborate 、 二乙基甲氧基硼烷 、 氢氟酸 、 氯化铵 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 29.0h， 生成 (1S,2S,4aR,6S,8S,8aS,4'R,6'R)-6'<2-<1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2'',2''-dimethylbutyryl)oxy>-6-<(E)-prop-1-enyl>-1-naphthalenyl>ethyl>tetrahydro-4'-hydroxy-2'H-pyran-2'-one
  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 、 chromium dichloride 、 4-二甲氨基吡啶 、 lithium hydroxide 、 重铬酸吡啶 、 3 A molecular sieve 、 sodium hexamethyldisilazane 、 三乙基硼氢化锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 218.33h， 生成 methyl (1S,2S,4aR,6S,8S,8aS,3'R)-7-<1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2'',2''-dimethyl-1''-oxobutyl)oxy>-6-<(E)-prop-1-enyl>-1-naphthalenyl>-3'-<(tert-butyldimethylsilyl)oxy>-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

• An improved procedure for the introduction of the .delta.-lactone portion of HMG-CoA 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/jo00032a062

  日期：1992.3
• 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.