N-benzoyl-D-leucine methyl 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: N-benzoyl-D-leucine methyl ester
• 英文别名: methyl (2R)-2-benzamido-4-methylpentanoate
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: BWMCGUZUOFOKJF-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoroethyl(mesityl)iodonium trifluoromethanesulfonate 、 N-benzoyl-D-leucine methyl ester 在 palladium diacetate 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以65%的产率得到methyl (2-(2,2,2-trifluoroethyl)benzoyl)-D-leucinate
  参考文献：
  名称：

  钯催化芳酰胺的直接C–H三氟乙基化

  摘要：

  已开发出一种简单直接的芳族酰胺CH–H三氟乙基化方法。该协议适用于多种芳香酰胺，包括衍生自氨基酸的芳香酰胺。所开发的方法可以用于肽的进一步修饰。通过分离反应中间体进行了初步的机理研究。

  DOI：

  10.1021/acs.orglett.7b01859
• 作为产物：
  描述：

  DL-亮氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-benzoyl-L-leucine methyl ester 、 N-benzoyl-D-leucine methyl ester
  参考文献：
  名称：

  一种新型的α-酮酸催化不对称氨基转移的手性吡啶氧胺

  摘要：

  通过多步合成已经开发了一种新型的带有相邻手性立体中心的手性吡ido胺。吡ido胺在非常温和的条件下，在α-酮酸的不对称转氨反应中显示出催化活性，从而以27-78％的产率提供了34-62％ee的多种光学活性氨基酸。这项工作提供了使用溴吡啶7作为关键合成子来构建新的手性吡ido胺的合成策略，也代表了手性吡x胺在不对称催化中的早期应用实例。

  DOI：

  10.1016/j.tetlet.2016.09.005

文献信息

• Application of the addition of triorganozincates to N-(tert-butanesulfinyl)imines to the enantioselective synthesis of α-amino acids
  作者：Raquel Almansa、David Guijarro、Miguel Yus

  DOI：10.1016/j.tetlet.2009.05.008

  日期：2009.7

  Highly enantiomerically enriched N-protected α-amino acids can be easily prepared from optically pure N-(tert-butanesulfinyl)imines by a four-step sequence involving: diastereoselective addition of a triorganozincate to the imine, removal of the sulfinyl group, benzoylation of the nitrogen atom of the obtained primary amine and oxidation of one of the substituents on the carbon atom α to the nitrogen

  高度对映体富集的N-保护的α-氨基酸可以很容易地由光学纯的N-（叔丁烷亚磺酰基）亚胺通过以下四个步骤序列制得：非对映选择性地向亚胺中添加三有机锌，亚磺酰基的去除，苯甲酰基的苯甲酰化获得的伯胺的氮原子被碳原子α上的取代基之一氧化成氮。在亚磺酰基手性助剂中使用相同的配置，具有（R）或（S可以通过选择亚胺和有机锌酸盐的适当组合来制备构型。具有高光学纯度的α，α-二取代的α-氨基酯也可以通过将三烷基锌酸酯非对映选择性地加成到α-亚氨基酯中来制备。
• Cobalt‐Catalyzed Asymmetric Deuteration of α‐Amidoacrylates for Stereoselective Synthesis of α,β‐Dideuterated α‐Amino Acids
  作者：Aibo Li、Xinjian Song、Qiao Ren、Peiwang Bao、Xinyu Long、Fuli Huang、Lvjiang Yuan、Jianrong Steve Zhou、Xurong Qin

  DOI：10.1002/anie.202301091

  日期：——

  A cobalt-catalyzed enantioselective deuteration provides α,β-dideuterio-α-amino acids in excellent enantioselectivity and almost complete deuteration, using deuterated methanol as cheap deuterium source.

  使用氘化甲醇作为廉价的氘源，钴催化的对映选择性氘化以优异的对映选择性和几乎完全的氘化提供 α,β-二氘-α-氨基酸。
• Peptide-Catalyzed Conversion of Racemic Oxazol-5(4<i>H</i>)-ones into Enantiomerically Enriched α-Amino Acid Derivatives
  作者：Anthony J. Metrano、Scott J. Miller

  DOI：10.1021/jo402828f

  日期：2014.2.21

  We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.
• Enzymic asymmetric synthesis of .alpha.-amino acids. Enantioselective cleavage of 4-substituted oxazolin-5-ones and thiazolin-5-ones
  作者：Joyce Z. Crich、Rosario Brieva、Peer Marquart、Rui Lin Gu、Steffen Flemming、Charles J. Sih

  DOI：10.1021/jo00064a010

  日期：1993.6

  A general enzymatic asymmetric synthesis of L-alpha-amino acids has been developed. This method entails the use of the Pseudomonas cepacia lipase (P-30) to catalyze the enantioselective methanolysis of a variety of 4-substituted 2-phenyloxazolin-5-one derivatives in a nonpolar organic solvent to furnish optically-active N-benzoyl-L-alpha-amino acid methyl esters (ee = 66-98%), which in turn is subjected to a protease-catalyzed kinetic resolution yielding enantiomerically-pure N-benzoyl-L-alpha-amino acids. This synergistic coupling of two enzymes allows the ready preparation of L-alpha-amino acids of high enantiopurity in yields greater than 50%, an inherent advantage over conventional resolution procedures. Two proteases were found to catalyze the enantioselective hydrolysis of a variety of 4-substituted 2-phenylthiazolin-5-one derivatives to give N-(thiobenzoyl)-L-alpha-amino acids of high optical purity.
• Enantioselective Benzoylation of α-Amino Esters Using (<i>S</i>)-1-Benzoyl-2- (α-acetoxyethyl)benzimidazole, a Chiral Benzimidazolide
  作者：Anil V. Karnik、Suchitra S. Kamath

  DOI：10.1021/jo070962p

  日期：2007.9.1

  [GRAPHICS]A new chiral benzimidazolide is developed as a nonenzymatic acylating agent for enantioselective benzoylation of racemic cc-amino esters. The process is highly efficient, which exhibits uniformly high enantioselectivity for alpha-amino esters with or without aryl substituents under mild reaction conditions. The chiral benzimidazolide is inexpensive and is easily accessible.