(2R,3S)-2-amino-3-hydroxy-4,4,4-trifluorobutanoic acid | 135268-35-8

• 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: (2R,3S)-2-amino-3-hydroxy-4,4,4-trifluorobutanoic acid
• 英文别名: anti-(2R,3S)-4,4,4-trifluorothreonine；(2R,3S)-4,4,4-trifluoro-allo-threonine；(2R,3S)-4,4,4-trifluorothreonine；(2R,3S)-2-amino-4,4,4-trifluoro-3-hydroxybutanoic acid
• CAS: 135268-35-8
• 化学式: C₄H₆F₃NO₃
• 分子量: 173.092
• InChiKey: ITYVCUQVLKIGEY-NCGGTJAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2R,3S)-2-[(4S,5R)-4,5-diphenyloxazolidin-2-on-3-yl]-5,5-dimethyl-3-trifluoromethyl-4-oxapentan-5-olide 在 5%-palladium/activated carbon 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以97%的产率得到(2R,3S)-2-amino-3-hydroxy-4,4,4-trifluorobutanoic acid
  参考文献：
  名称：

  A practical synthesis of enantiopure 4,4,4-trifluoro-allo-threonine from an easily available fluorinated building block

  摘要：

  A practical method to prepare enantiopure 4,4,4-trifluoro-allo-threonine was developed by using an easily available fluorinated building block and a chiral auxiliary as starting materials. Trifluoroacetic anhydride was annulated with a ketene, derived from a glycine equivalent bearing a chiral oxazolidinone [(4S,5R)-4,5-diphenyloxazolidin-2-one], and acetone to afford a trifluoromethylated alpha,beta-unsaturated lactone. The asymmetric hydride reduction of the alpha,beta-unsaturated lactone proceeded with excellent stereoselectivity to give the corresponding (2R,3S)-4-oxapentan-5-olide derivative exclusively (diastereopurity, 99%). From the reduced product thus obtained, protecting groups were readily removed by acid treatment and subsequent catalytic hydrogenolysis to afford enantiopure (2R,35)-4,4,4-trifluoro-allo-threonine in an excellent yield (7 steps, 51% overall yield). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.041

文献信息

• Asymmetric Synthesis of Both Enantiomers of <i>a</i><i>nti</i>-4,4,4-Trifluorothreonine and 2-Amino-4,4,4-trifluorobutanoic Acid
  作者：Zhong-Xing Jiang、Ying-Ying Qin、Feng-Ling Qing

  DOI：10.1021/jo0344384

  日期：2003.9.1

  A short and efficient enantioselective synthesis of both enantiomers of anti-4,4,4-trifluorothreonine and 2-amino-4,4,4-trifluorobutanoic acid was successfully developed. Trifluoromethylation of benzyl-protected bromoalkene 4 provided key intermediate trifluoromethylated trans-disubstituted alkene 2 in good yield. The sequence then involved Sharpless asymmetric dihydroxylation, nucleophilic opening

  成功开发了一种短而有效的对映体，其合成抗4,4,4-三氟苏氨酸和2-氨基-4,4,4-三氟丁酸的对映体。苄基保护的溴代烯烃4的三氟甲基化以良好的收率提供了关键的中间体三氟甲基化的反式二取代烯烃2。然后，该序列涉及Sharpless不对称二羟基化，环状硫酸盐与NaN（3）的亲核打开，钯催化的选择性氢化和氧化。
• Stereocontrolled synthesis of 4,4,4-trifluorothreonine
  作者：Tomoya Kitazume、Jenq Tain Lin、Takashi Yamazaki

  DOI：10.1016/s0957-4166(00)80041-5

  日期：1991.1

  Stereoisomers of unnatural 4,4,4-trifluorothreonine are obtained through enzymatic resolution, and the absolute configuration of these materials is determined. 4,4,4-Trifluorothreonine thus prepared was evaluated for antifungal or antitumor activity.