(4R,5S)-5-{(S)-1-[((1S,2R)-2-Hydroxy-1-methoxycarbonyl-propyl)-methyl-carbamoyl]-ethyl}-4-methyl-2-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester | 197146-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R,5S)-5-{(S)-1-[((1S,2R)-2-Hydroxy-1-methoxycarbonyl-propyl)-methyl-carbamoyl]-ethyl}-4-methyl-2-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS: 197146-87-5
• 化学式: C₂₄H₃₆N₂O₇
• 分子量: 464.559
• InChiKey: CBYBENWTJHKTIB-SVQDAYRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  105.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (4R,5S)-5-{(S)-1-[((1S,2R)-2-Hydroxy-1-methoxycarbonyl-propyl)-methyl-carbamoyl]-ethyl}-4-methyl-2-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 60.0 ℃ 、101.32 kPa 条件下， 反应 4.0h， 以87%的产率得到N-[4(R)-(tert-butyloxycarbonyl)amino-3(S)-hydroxy-2(S)-methylpentanoyl]-N-methyl-L-threonine methyl ester
  参考文献：
  名称：

  N-methyl threonine analogues of deglycobleomycin A2: Synthesis and evaluation

  摘要：

  The synthesis of 5 and its D-allo-threonine epimer 6 and the comparison of their DNA cleavage efficiency and selectivity with that of deglycobleomycin A(2) (3) are detailed. The studies illustrate that N-methylation of the L-threonine subunit within deglycobleomycin A(2) dramatically reduces the DNA cleavage efficiency (10-15-fold), weakens and nearly abolishes the inherent DNA cleavage selectivity, but has little effect on the inherent oxidation capabilities of the activated Fe(III) complexes. The results are consistent with a previously unrecognized prominent role for the threonine NH and the potential importance of a hydrogen bond to the Fe(III) hydroperoxide complex of bleomycin or a subsequent activated complex implicated in recent structural models. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00107-7
• 作为产物：
  描述：

  N-benzyl-N-methyl-L-threonine methyl ester 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 13.5h， 生成 (4R,5S)-5-{(S)-1-[((1S,2R)-2-Hydroxy-1-methoxycarbonyl-propyl)-methyl-carbamoyl]-ethyl}-4-methyl-2-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  N-methyl threonine analogues of deglycobleomycin A2: Synthesis and evaluation

  摘要：

  The synthesis of 5 and its D-allo-threonine epimer 6 and the comparison of their DNA cleavage efficiency and selectivity with that of deglycobleomycin A(2) (3) are detailed. The studies illustrate that N-methylation of the L-threonine subunit within deglycobleomycin A(2) dramatically reduces the DNA cleavage efficiency (10-15-fold), weakens and nearly abolishes the inherent DNA cleavage selectivity, but has little effect on the inherent oxidation capabilities of the activated Fe(III) complexes. The results are consistent with a previously unrecognized prominent role for the threonine NH and the potential importance of a hydrogen bond to the Fe(III) hydroperoxide complex of bleomycin or a subsequent activated complex implicated in recent structural models. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00107-7