Butanoic acid, 2-hydroxy-3-methyl-, 2-(trimethylsilyl)ethyl ester, (S)- | 185448-87-7

• 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: Butanoic acid, 2-hydroxy-3-methyl-, 2-(trimethylsilyl)ethyl ester, (S)-
• 英文别名: 2-trimethylsilylethyl (2S)-2-hydroxy-3-methylbutanoate
• CAS: 185448-87-7
• 化学式: C₁₀H₂₂O₃Si
• 分子量: 218.368
• InChiKey: CDANEXXWUCMROT-VIFPVBQESA-N

物化性质

• 沸点：
  259.9±15.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Butanoic acid, 2-hydroxy-3-methyl-, 2-(trimethylsilyl)ethyl ester, (S)- 在 盐酸 、 4-二甲氨基吡啶 、 异丙烯基氯甲酸酯 、 四丁基氟化铵 、 silica gel 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.75h， 生成 Me-Tyr(Bn)-OVal-N(Me)Val-OVal-D-N(Me)Trp-OOrn(Cbz)(Cbz)-OH
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of a Depsipeptide Mimic of Tendamistat

  摘要：

  The cyclic hexadepsipeptide framework of enniatin B was identified as a template matching the beta-turn tripeptide of tendamistat. The modified analog 1 was synthesized as a tendamistat mimic and compared to the acyclic derivative 2 and the tripeptide Ac-Try-Arg-Tyr-OMe. These compounds were assembled from the dimeric esters 3-5. As an inhibitor of alpha-amylase, 1 is twice as potent as 2 and comparable to the tripeptide. NMR studies of 1 reveal four conformers in equilibrium in a 50:25:15:10 ratio; the ring conformation of the major component is similar to that of the enniatin B template, with the cis geometry of the alpha-hydroxyisovaleryl-N-methylvaline amide linkage; the other conformers differ in the position or presence of the cis amide linkage.

  DOI：

  10.1021/jo9616062
• 作为产物：
  描述：

  (S)-2-benzyloxy-3-methylbutanoic acid 在 4-二甲氨基吡啶 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 Butanoic acid, 2-hydroxy-3-methyl-, 2-(trimethylsilyl)ethyl ester, (S)-
  参考文献：
  名称：

  使用埃文斯-季申科反应作为关键步骤进行Hoiamide A的全合成

  摘要：

  已经完成了神经毒性的环二肽hoiamide A（1）的第一个全合成。合成的特征是在含有五个立体中心的β-羟基酮与苏氨酸衍生的手性醛之间使用Evans-Tishchenko片段偶联。

  DOI：

  10.1021/acs.orglett.9b01735

文献信息

• Design, Synthesis, and Evaluation of a Depsipeptide Mimic of Tendamistat
  作者：Andrea M. Sefler、Marisa C. Kozlowski、Tao Guo、Paul A. Bartlett

  DOI：10.1021/jo9616062

  日期：1997.1.1

  The cyclic hexadepsipeptide framework of enniatin B was identified as a template matching the beta-turn tripeptide of tendamistat. The modified analog 1 was synthesized as a tendamistat mimic and compared to the acyclic derivative 2 and the tripeptide Ac-Try-Arg-Tyr-OMe. These compounds were assembled from the dimeric esters 3-5. As an inhibitor of alpha-amylase, 1 is twice as potent as 2 and comparable to the tripeptide. NMR studies of 1 reveal four conformers in equilibrium in a 50:25:15:10 ratio; the ring conformation of the major component is similar to that of the enniatin B template, with the cis geometry of the alpha-hydroxyisovaleryl-N-methylvaline amide linkage; the other conformers differ in the position or presence of the cis amide linkage.
• Total Synthesis of Hoiamide A Using an Evans–Tishchenko Reaction as a Key Step
  作者：Yian Guo、Jingjing Zhou、Bowen Gao、Meng Zhao、Jia-Lei Yan、Zhengshuang Xu、Sun Choi、Tao Ye

  DOI：10.1021/acs.orglett.9b01735

  日期：2019.7.19

  The first total synthesis of neurotoxic cyclodepsipeptide hoiamide A (1) has been accomplished. The synthesis features the use of an Evans–Tishchenko fragment coupling between a five-stereogenic-center-containing β-hydroxyketone and a chiral aldehyde derived from threonine.

  已经完成了神经毒性的环二肽hoiamide A（1）的第一个全合成。合成的特征是在含有五个立体中心的β-羟基酮与苏氨酸衍生的手性醛之间使用Evans-Tishchenko片段偶联。