(3S,5S)-3-<2'(E),4'-pentadienyl>-5-((tert-butyldiphenylsiloxy)methyl)tetrahydrofuran-2-one | 1026503-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,5S)-3-<2'(E),4'-pentadienyl>-5-((tert-butyldiphenylsiloxy)methyl)tetrahydrofuran-2-one
• 英文别名: (3S,5S)-3-(2'(E),4'-pentadienyl)-5-[(tert-butyldiphenylsiloxy)methyl]tetrahydrofuran-2-one；(3S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(2E)-penta-2,4-dienyl]oxolan-2-one
• CAS: 1026503-28-5
• 化学式: C₂₆H₃₂O₃Si
• 分子量: 420.624
• InChiKey: JHCWTJMCNDNGSN-HMUBQBSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,5S)-3-<2'(E),4'-pentadienyl>-5-((tert-butyldiphenylsiloxy)methyl)tetrahydrofuran-2-one 在 草酰氯 、 2,6-二叔丁基-4-甲基苯酚 、 四丁基氟化铵 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 均三甲苯 为溶剂， 反应 284.33h， 生成 (1S,4aR,6S,8S,8aS)-1-(ethoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-6,8-naphthalenecarbolactone
  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：

  (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 在 吡啶 、 sodium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 20.5h， 生成 (3S,5S)-3-<2'(E),4'-pentadienyl>-5-((tert-butyldiphenylsiloxy)methyl)tetrahydrofuran-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