(3S)-4-{butyl-[(1R)-1-(ethoxycarbonylmethyl-carbamoyl)-3-methyl-butyl]carbamoyl}-3-phenyl-butyric acid ethyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S)-4-{butyl-[(1R)-1-(ethoxycarbonylmethyl-carbamoyl)-3-methyl-butyl]carbamoyl}-3-phenyl-butyric acid ethyl ester
• 英文别名: ethyl (3S)-5-[butyl-[(2R)-1-[(2-ethoxy-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]amino]-5-oxo-3-phenylpentanoate
• 化学式: C₂₇H₄₂N₂O₆
• 分子量: 490.64
• InChiKey: GETMSTAALVADQH-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-亮氨酸 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 氯甲酸乙酯 、 sodium cyanoborohydride 、 1-羟基苯并三唑 、 sodium sulfate 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 29.67h， 生成 (3S)-4-{butyl-[(1R)-1-(ethoxycarbonylmethyl-carbamoyl)-3-methyl-butyl]carbamoyl}-3-phenyl-butyric acid ethyl ester
  参考文献：
  名称：

  Circular dichroism studies on absolute configuration assignment of peptidomimetics with a terminal chiral 3-arylpropionic acid unit

  摘要：

  The relationship between the molecular structure of peptidomimetics 1 and their chiroptical properties has been studied using circular dichroism spectroscopy. It was demonstrated that the sign of the Cotton effects occurring around 230 and 270 nm enables the direct assignment of stereochemistry at C-1 and C-3 carbon atoms. The TD-DFT calculations of the circular dichroisin (CD) spectrum of one of the model compounds confirm the absolute stereochemistry assignment made experimentally. Thus, CD spectroscopy proved to be a simple, reliable and general tool for the determination of the absolute configuration of the stereogenic centers of peptidomimetics with a terminal 3-arylpropionic group. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.024

文献信息

• One-pot enzymatic desymmetrization and Ugi MCR
  作者：Anna Fryszkowska、Jadwiga Frelek、Ryszard Ostaszewski

  DOI：10.1016/j.tet.2005.04.032

  日期：2005.6

  A new approach to the synthesis of chiral peptidomimetics is reported. It combines an enzymatic desymmetrization of 3-phenylglutaric anhydrides with a subsequent Ugi multi-component reaction in a one-pot, two-step procedure. NMR and CD spectroscopy was used to assign the configurations of obtained products. Our synthetic method is very efficient and it can easily be extended to other types of multi-component reactions and can be used for the preparation of chiral peptidomimetic libraries. (c) 2005 Elsevier Ltd. All rights reserved.