(S)-2-[(S)-3-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-1-trifluoromethyl-propylamino]-N-benzyloxy-3-methyl-butyramide | 347383-72-6

• 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: (S)-2-[(S)-3-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-1-trifluoromethyl-propylamino]-N-benzyloxy-3-methyl-butyramide
• 英文别名: (2S)-2-[[(2S)-4-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-1,1,1-trifluoro-4-oxobutan-2-yl]amino]-3-methyl-N-phenylmethoxybutanamide
• CAS: 347383-72-6
• 化学式: C₂₆H₃₀F₃N₃O₅
• 分子量: 521.537
• InChiKey: CXXAQKIASSUAQB-FUDKSRODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-2-[(S)-3-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-1-trifluoromethyl-propylamino]-N-benzyloxy-3-methyl-butyramide 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以60%的产率得到(3S)-4,4,4-trifluoro-3-[[(2S)-3-methyl-1-oxo-1-(phenylmethoxyamino)butan-2-yl]amino]butanoic acid
  参考文献：
  名称：

  10.1002/1099-0690(20022)2002:3<428::aid-ejoc428<3.0.co;2-j

  摘要：

  DOI：

  10.1002/1099-0690(20022)2002:3<428::aid-ejoc428<3.0.co;2-j
• 作为产物：
  描述：

  (4S)-benzyl-3-[(E)-4,4,4-trifluorobut-2-enoyl]-oxazolidin-2-one 、 valine hydroxamic acid benzyl ester mono TFA salt 在 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (S)-2-[(S)-3-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-1-trifluoromethyl-propylamino]-N-benzyloxy-3-methyl-butyramide 、 (S)-2-[(R)-3-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-1-trifluoromethyl-propylamino]-N-benzyloxy-3-methyl-butyramide
  参考文献：
  名称：

  Solution/solid-phase synthesis of partially modified retro- ψ [NHCH(CF 3 )]-peptidyl hydroxamates

  摘要：

  The synthesis of a novel family of partially-modified (PM) retropeptidyl hydroxamates incorporating a [CH(CF3)CH2CO] unit as a surrogate of the conventional malonyl group, has been accomplished both in solution and in solid-phase. The key step is the Michael-type N-addition of free or polymer bound alpha -amino hydroxamates to 3-(E-enoyl)-1,3-oxazolidin-2-ones, which takes place very effectively, although with low stereocontrol. A number of tri- and tetra-peptidyl hydroxamates were obtained either in diastereomerically pure form (by solution-phase synthesist after chromatographic purification), or as mixtures of two epimers in very good chemical purity (by solid-phase, after release from the resin), demonstrating that this method is suitable for preparing combinatorial libraries of PM retro-psi [NHCH(CF3)]-peptidyl hydroxamates for screening as metalloprotease inhibitors. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00375-6