[2S,4R]-(-)-2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoic acid | 362495-90-7

• 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: [2S,4R]-(-)-2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoic acid
• 英文别名: (2S,4R)-2-methyl-4-(p-toluenesulfonylamino)-5-phenylpentanoic acid；(2S,4R)-2-methyl-4-[(4-methylphenyl)sulfonylamino]-5-phenylpentanoic acid
• CAS: 362495-90-7
• 化学式: C₁₉H₂₃NO₄S
• 分子量: 361.462
• InChiKey: VDUQDBHPRVOPPB-DOTOQJQBSA-N

物化性质

• 沸点：
  572.1±60.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2S,4R]-(-)-2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoic acid 在 盐酸 、 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 methyl (2S,4R)-4-[(tert-butoxycarbonyl)(p-toluenesulfonyl)amino]-2-methyl-5-phenylpentanoate
  参考文献：
  名称：

  U和V的微管溶素的全合成。

  摘要：

  DOI：

  10.1002/anie.200601259
• 作为产物：
  描述：

  S)-(+)- 2-苄基- 1-（对甲苯磺酰）氮丙啶 在 硫酸 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 [2S,4R]-(-)-2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoic acid
  参考文献：
  名称：

  Aziridine Ring-Opening Reactions with Chiral Enolates. Stereocontrolled Synthesis of 5-Substituted-3-methyl-pyrrolidin-2-ones

  摘要：

  A procedure for performing stereocontrolled aziridine ring-opening reactions with chiral enolates derived from (S,S)-(+)-pseudoephedrine amides has been developed leading to gamma -aminoamides in good yields. The diastereoselectivity of the reaction becomes controlled by the presence of the chiral auxiliary on the enolate, although the stereogenic center contained in the structure of the aziridine has a striking influence on the stereochemical course of the reaction which results in the presence of the corresponding matched and mismatched combinations. Besides, the sense of the asymmetric induction of the chiral auxiliary has resulted to be the opposite to the one found with other type of electrophiles, although it is in good agreement with the trend observed in the reaction of the same kind of enolates with epoxides. Finally, the obtained gamma -aminoamide adducts were converted into enantiopure gamma -amino acids, gamma -aminoesters, and pyrrolidin-2-ones using easy to perform and high yielding reactions.

  DOI：

  10.1021/jo0103571

文献信息

• Total Synthesis of Tubulysin U and V
  作者：Alexander Dömling、Barbara Beck、Uwe Eichelberger、Sukumar Sakamuri、Sanjay Menon、Quin-Zene Chen、Yingchun Lu、Ludger A. Wessjohann

  DOI：10.1002/anie.200601259

  日期：2006.11.6
• Aziridine Ring-Opening Reactions with Chiral Enolates. Stereocontrolled Synthesis of 5-Substituted-3-methyl-pyrrolidin-2-ones
  作者：Jose L. Vicario、Dolores Badía、Luisa Carrillo

  DOI：10.1021/jo0103571

  日期：2001.8.1

  A procedure for performing stereocontrolled aziridine ring-opening reactions with chiral enolates derived from (S,S)-(+)-pseudoephedrine amides has been developed leading to gamma -aminoamides in good yields. The diastereoselectivity of the reaction becomes controlled by the presence of the chiral auxiliary on the enolate, although the stereogenic center contained in the structure of the aziridine has a striking influence on the stereochemical course of the reaction which results in the presence of the corresponding matched and mismatched combinations. Besides, the sense of the asymmetric induction of the chiral auxiliary has resulted to be the opposite to the one found with other type of electrophiles, although it is in good agreement with the trend observed in the reaction of the same kind of enolates with epoxides. Finally, the obtained gamma -aminoamide adducts were converted into enantiopure gamma -amino acids, gamma -aminoesters, and pyrrolidin-2-ones using easy to perform and high yielding reactions.