(+)-(3S,5S)-3-<2'(E),4'(E)-hexadienyl>-5-((tert-butyldiphenylsiloxy)methyl)tetrahydrofuran-2-one | 116097-22-4

• 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'(E)-hexadienyl>-5-((tert-butyldiphenylsiloxy)methyl)tetrahydrofuran-2-one
• 英文别名: (+)-(3S,5S)-3-(2'(E),4'(E)-hexadienyl)-5-[(tert-butyldiphenylsiloxy)methyl]tetrahydrofuran-2-one；(3S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-[(2E,4E)-hexa-2,4-dienyl]oxolan-2-one
• CAS: 116097-22-4；116180-68-8
• 化学式: C₂₇H₃₄O₃Si
• 分子量: 434.651
• InChiKey: UYLFTIUTGMHCNS-JKPLPFGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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'(E)-hexadienyl>-5-((tert-butyldiphenylsiloxy)methyl)tetrahydrofuran-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以91%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
• 作为产物：
  描述：

  sorbyl bromide 在 溴代叔丁烷 、 lithium hexamethyldisilazane 作用下， 反应 0.83h， 生成 (+)-(3S,5S)-3-<2'(E),4'(E)-hexadienyl>-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

文献信息

• The enantiospecific synthesis of dihydromevinolin from L-glutamic acid
  作者：Alan H. Davidson、Andrew J. Jones、Chris D. Floyd、Christopher Lewis、Peter L. Myers

  DOI：10.1039/c39870001786

  日期：——

  An enantiospecific synthesis of the diol (3), a compound which has previously been converted into dihydromevinolin, is reported.

  据报道二醇（3）的对映体特异性合成，该化合物先前已被转化为二氢甲基乙烯基。
• 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.