1-benzyl-4-tert-butyl(2R,3S)-2-[4-(benzyloxy)benzyl]-3-(3-{[(4-nitrophenoxy)carbonyl]oxy}propyl)butanedioate | 377088-77-2

• 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: 1-benzyl-4-tert-butyl(2R,3S)-2-[4-(benzyloxy)benzyl]-3-(3-{[(4-nitrophenoxy)carbonyl]oxy}propyl)butanedioate
• 英文别名: 4-O-benzyl 1-O-tert-butyl (2S,3R)-2-[3-(4-nitrophenoxy)carbonyloxypropyl]-3-[(4-phenylmethoxyphenyl)methyl]butanedioate
• CAS: 377088-77-2
• 化学式: C₃₉H₄₁NO₁₀
• 分子量: 683.755
• InChiKey: JFJXKMYKNUJSDK-OIDHKYIRSA-N

物化性质

• 沸点：
  770.5±60.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-tert-butyl(2R,3S)-2-[4-(benzyloxy)benzyl]-3-(3-{[(4-nitrophenoxy)carbonyl]oxy}propyl)butanedioate 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 12-tert-butyl-8-methyl(8S,11R,12S)-11-(4-hydroxybenzyl)-2,10-dioxo-1-oxa-3,9-diazacyclopentadecane-8,12-dicarboxylate
  参考文献：
  名称：

  Discovery of Macrocyclic Hydroxamic Acids Containing Biphenylmethyl Derivatives at P1‘, a Series of Selective TNF-α Converting Enzyme Inhibitors with Potent Cellular Activity in the Inhibition of TNF-α Release

  摘要：

  SAR exploration at P1' using an anti-succinate-based macrocyclic hydroxamic acid as a template led to the identification of several bulky biphenylmethyl P1' derivatives which confer potent porcine TACE and anti-TNF-alpha cellular activities with high selectivity versus most of the MMPs screened. Our studies demonstrate for the first time that TACE has a larger S1' pocket in comparison to MMPs and that potent and selective TACE inhibitors can be achieved by incorporation of sterically bulky P1' residues.

  DOI：

  10.1021/jm0155502
• 作为产物：
  描述：

  3-[4-(苄氧基)苯基]丙酸 在 N-甲基吗啉 、 lithium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 正丁基锂 、 双氧水 、 氯化二乙基铝 、 三甲基乙酰氯 、 二异丙胺 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 1-benzyl-4-tert-butyl(2R,3S)-2-[4-(benzyloxy)benzyl]-3-(3-{[(4-nitrophenoxy)carbonyl]oxy}propyl)butanedioate
  参考文献：
  名称：

  Discovery of Macrocyclic Hydroxamic Acids Containing Biphenylmethyl Derivatives at P1‘, a Series of Selective TNF-α Converting Enzyme Inhibitors with Potent Cellular Activity in the Inhibition of TNF-α Release

  摘要：

  SAR exploration at P1' using an anti-succinate-based macrocyclic hydroxamic acid as a template led to the identification of several bulky biphenylmethyl P1' derivatives which confer potent porcine TACE and anti-TNF-alpha cellular activities with high selectivity versus most of the MMPs screened. Our studies demonstrate for the first time that TACE has a larger S1' pocket in comparison to MMPs and that potent and selective TACE inhibitors can be achieved by incorporation of sterically bulky P1' residues.

  DOI：

  10.1021/jm0155502