(3S,5S)-3-((2E,4E)-Hexa-2,4-dienyl)-5-trityloxymethyl-dihydro-furan-2-one | 143633-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (3S,5S)-3-((2E,4E)-Hexa-2,4-dienyl)-5-trityloxymethyl-dihydro-furan-2-one
• 英文别名: (3S,5S)-3-[(2E,4E)-hexa-2,4-dienyl]-5-(trityloxymethyl)oxolan-2-one
• CAS: 143633-53-8
• 化学式: C₃₀H₃₀O₃
• 分子量: 438.566
• InChiKey: AXCJHHXCRPNZTG-SRVBUPDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 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-((2E,4E)-Hexa-2,4-dienyl)-5-trityloxymethyl-dihydro-furan-2-one 在 甲醇 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以82%的产率得到(+)-(3S,5S)-3-<2'(E),4'(E)-hexadienyl>-5-(hydroxymethyl)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

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.