Oxalic acid (S)-3-benzyloxycarbonylamino-3-tert-butoxycarbonyl-1,1-bis-trifluoromethyl-propyl ester phenyl ester | 1053719-24-6

• 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: Oxalic acid (S)-3-benzyloxycarbonylamino-3-tert-butoxycarbonyl-1,1-bis-trifluoromethyl-propyl ester phenyl ester
• 英文别名: 1-O-phenyl 2-O-[(4S)-1,1,1-trifluoro-5-[(2-methylpropan-2-yl)oxy]-5-oxo-4-(phenylmethoxycarbonylamino)-2-(trifluoromethyl)pentan-2-yl] oxalate
• CAS: 1053719-24-6
• 化学式: C₂₆H₂₅F₆NO₈
• 分子量: 593.477
• InChiKey: OPSGWEUOTCEEFI-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Oxalic acid (S)-3-benzyloxycarbonylamino-3-tert-butoxycarbonyl-1,1-bis-trifluoromethyl-propyl ester phenyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 、 potassium fluoride 作用下， 以 甲苯 、 乙醚 为溶剂， 反应 3.08h， 生成 tert-butyl (2S)-2-[[(benzyloxy)carbonyl]amino]-5,5,5-trifluoro-4-(trifluoromethyl)pentanoate
  参考文献：
  名称：

  A Short and Efficient Synthesis of l-5,5,5,5‘,5‘,5‘-hexafluoroleucine from N-Cbz-l-Serine

  摘要：

  [GRAPHICS]5,5,5,5',5',5'-Hexafluoroleucine (6), a fluorous analogue of leucine, is of considerable interest as a building block in the design of fluorous proteins and peptides. We report a short and efficient synthesis of 6, which is obtained from N-Cbz-L-serine (1) in 50% overall yield, 99% enantiomeric excess, and In multigram quantities. Key steps are addition of a serine-derived organozincate to hexafluoroacetone to construct the hexafluoroleucine side chain, followed by radical-mediated deoxygenation of the resulting tertiary alcohol.

  DOI：

  10.1021/ol026922j
• 作为产物：
  描述：

  2-benzyloxycarbonylamino-3-iodo-propionic acid tert-butyl ester 在 吡啶 、 三甲基氯硅烷 、 1,2-二溴乙烷 、 锌 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 Oxalic acid (S)-3-benzyloxycarbonylamino-3-tert-butoxycarbonyl-1,1-bis-trifluoromethyl-propyl ester phenyl ester
  参考文献：
  名称：

  A Short and Efficient Synthesis of l-5,5,5,5‘,5‘,5‘-hexafluoroleucine from N-Cbz-l-Serine

  摘要：

  [GRAPHICS]5,5,5,5',5',5'-Hexafluoroleucine (6), a fluorous analogue of leucine, is of considerable interest as a building block in the design of fluorous proteins and peptides. We report a short and efficient synthesis of 6, which is obtained from N-Cbz-L-serine (1) in 50% overall yield, 99% enantiomeric excess, and In multigram quantities. Key steps are addition of a serine-derived organozincate to hexafluoroacetone to construct the hexafluoroleucine side chain, followed by radical-mediated deoxygenation of the resulting tertiary alcohol.

  DOI：

  10.1021/ol026922j