S-ethyl (2S,3R)-3-hydroxy-2-methyl-5-phenylpentanethioate | 156039-18-8

• 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: S-ethyl (2S,3R)-3-hydroxy-2-methyl-5-phenylpentanethioate
• CAS: 156039-18-8
• 化学式: C₁₄H₂₀O₂S
• 分子量: 252.378
• InChiKey: WPGYIAYMADWKBN-WCQYABFASA-N

物化性质

• 沸点：
  393.4±35.0 °C(predicted)
• 密度：
  1.094±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-ethyl (2S,3R)-3-hydroxy-2-methyl-5-phenylpentanethioate 在 水 、 双氧水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以83%的产率得到(2S,3R)-3-hydroxy-2-methyl-5-phenylpentanoic acid
  参考文献：
  名称：

  MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin

  摘要：

  Various beta-lactones were prepared from beta-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

  DOI：

  10.1021/jo300139r
• 作为产物：
  描述：

  苯丙醛 、 (Z)-1-ethylthio-1-(trimethylsiloxy)propene 在 tin(II) trifluoromethanesulfonate 、 三正丁基氢锡 、 (S)-(-)-1-甲基-2-(1-萘氨基甲基)吡咯烷 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以52%的产率得到S-ethyl (2S,3R)-3-hydroxy-2-methyl-5-phenylpentanethioate
  参考文献：
  名称：

  MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin

  摘要：

  Various beta-lactones were prepared from beta-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

  DOI：

  10.1021/jo300139r

文献信息

• Diastereoselective Aldol and Reformatsky Reactions of<b><i>α</i></b>-Halo Carbonyl Compounds and Aldehydes Mediated by Titanium(II) Chloride
  作者：Akifumi Kagayama、Koji Igarashi、Isamu Shiina、Teruaki Mukaiyama

  DOI：10.1246/bcsj.73.2579

  日期：2000.11

  Highly diastereoselective aldol reactions of α-bromo ketones with several aldehydes were successfully carried out by using a combination of titanium(II) chloride and copper or sodium iodide in dichloromethane-pivalonitrile at low temperature. Similarly, Reformatsky reactions of α-bromo thioester with aliphatic aldehydes proceeded to afford β-hydroxy thioesters in good yields under mild conditions.

  通过在低温下在二氯甲烷-新戊腈中使用氯化钛 (II) 和碘化铜或碘化钠的组合，成功地进行了 α-溴酮与几种醛的高度非对映选择性羟醛反应。类似地，α-溴硫酯与脂肪醛的 Reformatsky 反应在温和条件下以良好的产率得到 β-羟基硫酯。
• The catalytic asymmetric aldol reaction of aldehydes with unsubstituted and monosubstituted silyl ketene acetals: formation of anti-β-hydroxy-α-methyl esters
  作者：Emma R. Parmee、Yaping Hong、Orin Tempkin、Satoru Masamune

  DOI：10.1016/s0040-4039(00)91717-9

  日期：1992.3

  The title reaction with unsubstituted and monosubstituted silyl ketene acetals proceeds with high enantioselectivity, and in the latter case good diastereoselectivity favoring the anti-β-hydroxy-α-methyl esters in all reported cases.

  与未取代和单取代的甲硅烷基乙烯酮缩醛的标题反应以高对映选择性进行，在后一种情况下，在所有报道的情况下，良好的非对映选择性有利于抗β-羟基-α-甲基酯。
• Facile removal of 4-phenyl-oxazolidinethione auxiliary with EtSH mediated by DBU
  作者：Yikang Wu、Qi Hu、Ya-Ping Sun、Yong-Qing Yang

  DOI：10.1016/j.tetlet.2004.08.113

  日期：2004.10

  In methylene chloride at OdegreesC N-acyl-beta-hydroxy-4-phenyl-oxazolidinethiones could be rapidly converted into corresponding ethyl thioesters in high yields by treatment with EtSH in the presence of a catalytic amount of DBU. (C) 2004 Elsevier Ltd. All rights reserved.