methyl (2R)-2-benzamido-4-methylsulfanylbutanoate

• 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: methyl (2R)-2-benzamido-4-methylsulfanylbutanoate
• 化学式: C₁₃H₁₇NO₃S
• 分子量: 267.349
• InChiKey: GDYWLOSEHSCOED-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 4-(2-methylsulfanyl-ethyl)-2-phenyl-4H-oxazol-5-one 在 planar-chiral DMAP-ferrocene derivative 、 苯甲酸 作用下， 以 甲苯 为溶剂， 生成 N-苯甲酰基-L-蛋氨酸甲酯 、 methyl (2R)-2-benzamido-4-methylsulfanylbutanoate
  参考文献：
  名称：

  Dynamic Kinetic Resolutions Catalyzed by a Planar-Chiral Derivative of DMAP:  Enantioselective Synthesis of Protected α-Amino Acids from Racemic Azlactones

  摘要：

  DOI：

  10.1021/jo9803380

文献信息

• 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.
• Dynamic Kinetic Resolutions Catalyzed by a Planar-Chiral Derivative of DMAP:  Enantioselective Synthesis of Protected α-Amino Acids from Racemic Azlactones
  作者：Jack Liang、J. Craig Ruble、Gregory C. Fu

  DOI：10.1021/jo9803380

  日期：1998.5.1
• Dynamic kinetic resolution: synthesis of optically active α-amino acid derivatives
  作者：Stuart A Brown、Marie-Claire Parker、Nicholas J Turner

  DOI：10.1016/s0957-4166(00)00108-7

  日期：2000.5

  Candida antarctica lipase B (Novozyme) is an effective catalyst for the dynamic kinetic resolution of racemic 2-benzyl-4-substituted-5(4H)-oxazolones, in the presence of an alcohol, yielding optically active N-benzoyl amino acid esters. The reaction has been optimised with respect to the solvent and the effect of a catalytic amount of organic base is investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.