(-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester | 948859-73-2

• 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: (-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester
• 英文别名: S-ethyl (E,5S)-6-[tert-butyl(diphenyl)silyl]oxy-5-methylhex-2-enethioate
• CAS: 948859-73-2
• 化学式: C₂₅H₃₄O₂SSi
• 分子量: 426.695
• InChiKey: PBLWVQPOQYCDLU-YMFQVDJJSA-N

物化性质

• 沸点：
  505.8±43.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester 在 palladium on activated charcoal 吡啶 、 三乙基硅烷 、 二异丁基氢化铝 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 272.02h， 生成 (-)-(2S,4S,6S,8S,10S,12S,14S)-tert-butyl-(2,4,6,8,10,12,14-heptamethyl-triacontyloxy)-diphenyl-silane
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Phthioceranic Acid, a Heptamethyl-Branched Acid from Mycobacterium tuberculosis

  摘要：

  The first total synthesis of phthioceranic acid (1) has been achieved by an iterative catalytic asymmetric 1,4-addition protocol. This method provides a robust and high-yielding route for the preparation of 1,3-oligomethyl (deoxypropionate) arrays. After the desired number of methyl groups has been introduced, these arrays can be further functionalized at both ends to polymethyl-substituted lipids such as phthioceranic acid, a heptamethyl-branched fatty acid from the virulence factor Sulfolipid-I (2), found in Mycobacterium tuberculosis.

  DOI：

  10.1021/ol071078o
• 作为产物：
  描述：

  2-(叔丁基二苯基硅氧基)乙醇 在 palladium on activated charcoal 三乙基硅烷 、 2-碘酰基苯甲酸 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 89.17h， 生成 (-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Phthioceranic Acid, a Heptamethyl-Branched Acid from Mycobacterium tuberculosis

  摘要：

  The first total synthesis of phthioceranic acid (1) has been achieved by an iterative catalytic asymmetric 1,4-addition protocol. This method provides a robust and high-yielding route for the preparation of 1,3-oligomethyl (deoxypropionate) arrays. After the desired number of methyl groups has been introduced, these arrays can be further functionalized at both ends to polymethyl-substituted lipids such as phthioceranic acid, a heptamethyl-branched fatty acid from the virulence factor Sulfolipid-I (2), found in Mycobacterium tuberculosis.

  DOI：

  10.1021/ol071078o

文献信息

• Formal Synthesis of the Anti-Angiogenic Polyketide (−)-Borrelidin under Asymmetric Catalytic Control
  作者：Ashoka V. R. Madduri、Adriaan J. Minnaard

  DOI：10.1002/chem.201001284

  日期：——

  potent anti‐angiogenesis activity. This paper describes its formal total synthesis by the most efficient route to date. This modular approach takes optimal benefit of asymmetric catalysis and permits the synthesis of analogues; in addition, the high yields and selectivities obtained eliminate the need for separation of stereoisomers. The upper half of borrelidin has been accessed by iterative copper‐catalysed

  硼瑞林（1）是一种聚酮化合物，具有极强的抗血管生成活性。本文通过迄今为止最有效的方法描述了其正式的全合成方法。这种模块化方法利用了不对称催化的最佳优势，并允许合成类似物。另外，获得的高产率和选择性消除了分离立体异构体的需要。硼氢化利丁的上半部分已通过铜催化的甲基溴的不对称共轭铜的迭代添加而获得，而分子下半部分的合成是通过不对称加氢和交叉甲基化作为关键步骤而实现的。
• Catalytic Asymmetric Synthesis of Mycolipenic and Mycolipanolic Acid
  作者：Bjorn ter Horst、Jeroen van Wermeskerken、Ben L. Feringa、Adriaan J. Minnaard

  DOI：10.1002/ejoc.200901120

  日期：2010.1

  The first asymmetric synthesis of mycolipenic acid and mycolipanolic acid by using an improved iterative procedure involving catalytic asymmetric conjugate addition of MeMgBr as the key step is described. Mycolipenic and mycolipanolic acid are obtained in 11 steps with perfect stereocontrol, and both acids are identical to their counterparts from natural sources.

  描述了通过使用改进的迭代程序，包括 MeMgBr 的催化不对称共轭加成作为关键步骤，首次不对称合成霉烯酸和霉烯酸。Mycolipenic 和 mycolipanolic 酸是通过 11 个步骤获得的，具有完美的立体控制，这两种酸与来自天然来源的对应物相同。