methyl (1S,2S,4aR,6S,8S,8aS,3'R,2''S)-3'-(tert-butyldimethylsiloxy)-7'-<2-methyl-8-<(2''-methylbutyryl)oxy>-1,2,4a,5,6,7,8,8a-octahydro-6-<(Z)-prop-1-enyl>-1-naphthalenyl>-5'-oxohept-6'-enoate | 134852-81-6

• 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'-<2-methyl-8-<(2''-methylbutyryl)oxy>-1,2,4a,5,6,7,8,8a-octahydro-6-<(Z)-prop-1-enyl>-1-naphthalenyl>-5'-oxohept-6'-enoate
• CAS: 134852-81-6；134932-94-8；143633-64-1
• 化学式: C₃₃H₅₄O₆Si
• 分子量: 574.874
• InChiKey: PYNWPUCERVWPIZ-VXEKOUIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.45
• 重原子数：
  40.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

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'-<2-methyl-8-<(2''-methylbutyryl)oxy>-1,2,4a,5,6,7,8,8a-octahydro-6-<(Z)-prop-1-enyl>-1-naphthalenyl>-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， 生成 methyl (3R,5R)-7-[(1S,2S,4aR,6S,8S,8aS)-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-6-[(Z)-prop-1-enyl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
  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,3S,4aR,6S,8S,8aS)-1-(tert-butyldimethylsiloxy)-1,2,3,4,4a,7,8,8a-octahydro-8-(hydroxymethyl)-7-methyl-3-<(Z)-prop-1-enyl>naphthalene 在 重铬酸吡啶 、 3 A molecular sieve 、 氢氟酸 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 95.0h， 生成 methyl (1S,2S,4aR,6S,8S,8aS,3'R,2''S)-3'-(tert-butyldimethylsiloxy)-7'-<2-methyl-8-<(2''-methylbutyryl)oxy>-1,2,4a,5,6,7,8,8a-octahydro-6-<(Z)-prop-1-enyl>-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