ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate | 116097-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate
• 英文别名: ethyl (1S,2S,4aR,6S,8S,8aS)-8-[tert-butyl(dimethyl)silyl]oxy-2-methyl-6-[(4-methylphenyl)sulfonyloxymethyl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate
• CAS: 116097-25-7
• 化学式: C₂₈H₄₄O₆SSi
• 分子量: 536.805
• InChiKey: HTRPWAYFGDOLBR-FWQMOCORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 生成 (+)-(1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-1-(hydroxymethyl)-2,6-dimethylnaphthalene
  参考文献：
  名称：

  从L-谷氨酸对映体合成二氢美诺灵

  摘要：

  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。

  DOI：

  10.1039/c39870001786
• 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 、 2,6-二甲基吡啶 、 N-[(2,4-二氯苯氧基)-甲氧基硫代膦酰]丙-2-胺 、 sodium hexamethyldisilazane 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 95.0h， 生成 ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate
  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.