(2S,3S,4S,6R)-2,4,6-trimethylheptane-1,3,7-triol | 124819-04-1

• 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: (2S,3S,4S,6R)-2,4,6-trimethylheptane-1,3,7-triol
• CAS: 124819-04-1
• 化学式: C₁₀H₂₂O₃
• 分子量: 190.283
• InChiKey: RUPLFPZWROYYDL-KATARQTJSA-N

物化性质

• 沸点：
  345.3±22.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,6R)-2,4,6-trimethylheptane-1,3,7-triol 在 咪唑 、 camphor-10-sulfonic acid 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 (2S,3S,4S,6R)-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-7-(tert-butyldimethylsilyloxy)heptan-1-ol
  参考文献：
  名称：

  Stereoselective Formal Total Synthesis of (+)-Methynolide

  摘要：

  A highly stereoselective and convergent formal total synthesis of (+)-methynolide is described. The salient features of this synthesis have been the construction of the C1-C7 and C8-C11fragments via a desymmetrization approach, Sharpless asymmetric epoxidation of an allyl alcohol, respectively, and linkage of both the fragments by Nozaki-Hiyama-Kishi reaction.

  DOI：

  10.1021/jo0704762
• 作为产物：
  描述：

  (2S,3R,4S)-5-benzyloxy-2,3-dimethylpentane-1,4-diol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 叔丁醇 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 104.5h， 生成 (2S,3S,4S,6R)-2,4,6-trimethylheptane-1,3,7-triol
  参考文献：
  名称：

  Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin

  摘要：

  A short and efficient total synthesis of 10-deoxymethynolide (2c), the aglycon of 10-deoxymethymycin (1c), has been accomplished in 16 steps and 12% overall yield from (S)-3-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (15c). The synthesis features an expeditious preparation of (+)-5a, a synthetic equivalent of the Prelog-Djerassi lactonic acid, and the construction of a 12-membered lactone through an intramolecular Nozaki-Hiyama-Kishi coupling reaction.

  DOI：

  10.1021/jo9809433

文献信息

• Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin
  作者：Ronaldo A. Pilli、Carlos Kleber Z. de Andrade、Carlos Roberto O. Souto、Armin de Meijere

  DOI：10.1021/jo9809433

  日期：1998.10.1

  A short and efficient total synthesis of 10-deoxymethynolide (2c), the aglycon of 10-deoxymethymycin (1c), has been accomplished in 16 steps and 12% overall yield from (S)-3-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (15c). The synthesis features an expeditious preparation of (+)-5a, a synthetic equivalent of the Prelog-Djerassi lactonic acid, and the construction of a 12-membered lactone through an intramolecular Nozaki-Hiyama-Kishi coupling reaction.
• Stereoselective Formal Total Synthesis of (+)-Methynolide
  作者：J. S. Yadav、T. V. Pratap、V. Rajender

  DOI：10.1021/jo0704762

  日期：2007.7.1

  A highly stereoselective and convergent formal total synthesis of (+)-methynolide is described. The salient features of this synthesis have been the construction of the C1-C7 and C8-C11fragments via a desymmetrization approach, Sharpless asymmetric epoxidation of an allyl alcohol, respectively, and linkage of both the fragments by Nozaki-Hiyama-Kishi reaction.