((S)-2-benzyl-3-methoxy-3-oxopropyl)((S)-1-(((benzyloxy)carbonyl)amino)-3-phenylpropyl)phosphinic acid | 920529-27-7

• 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: ((S)-2-benzyl-3-methoxy-3-oxopropyl)((S)-1-(((benzyloxy)carbonyl)amino)-3-phenylpropyl)phosphinic acid
• CAS: 920529-27-7
• 化学式: C₂₈H₃₂NO₆P
• 分子量: 509.539
• InChiKey: YAZZZDYDWAWXFU-FTJBHMTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101.93
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((S)-2-benzyl-3-methoxy-3-oxopropyl)((S)-1-(((benzyloxy)carbonyl)amino)-3-phenylpropyl)phosphinic acid 在 三甲基溴硅烷 、 盐酸 作用下， 反应 72.0h， 生成 (2s)-3-[(R)-[(1s)-1-Amino-3-Phenylpropyl](Hydroxy)phosphoryl]-2-Benzylpropanoic Acid
  参考文献：
  名称：

  Individual stereoisomers of phosphinic dipeptide inhibitor of leucine aminopeptidase

  摘要：

  Individual stereoisomers of the phosphinic pseudodipeptide hPhe psi P(O)(OH) CH2]Phe were obtained by stereoselective liquid chromatographic separation as N- and C-terminally protected derivative on quinidine carbamate modified silica stationary phase. The stereoisomeric purity, exceeding 95% for each fraction, was determined before and after deprotection using two independent methods. The absolute configuration was rationally assigned by application of enantiomerically pure phosphinic acid substrates in the synthetic procedure and correlation with biological activity of the products. Substantial differences in inhibition of leucine aminopeptidase by the individual isomers revealed novel insights into potency of the recently developed and remarkably effective compound. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.107
• 作为产物：
  描述：

  2-苄基丙烯酸甲酯 、 [1-(N-benzyloxycarbonylamino)-3-phenylpropyl]phosphinic acid 在 六甲基二硅氮烷 作用下， 反应 6.0h， 生成 ((S)-2-benzyl-3-methoxy-3-oxopropyl)((R)-1-(((benzyloxy)carbonyl)amino)-3-phenylpropyl)phosphinic acid 、 、 ((S)-2-benzyl-3-methoxy-3-oxopropyl)((S)-1-(((benzyloxy)carbonyl)amino)-3-phenylpropyl)phosphinic acid 、
  参考文献：
  名称：

  Individual stereoisomers of phosphinic dipeptide inhibitor of leucine aminopeptidase

  摘要：

  Individual stereoisomers of the phosphinic pseudodipeptide hPhe psi P(O)(OH) CH2]Phe were obtained by stereoselective liquid chromatographic separation as N- and C-terminally protected derivative on quinidine carbamate modified silica stationary phase. The stereoisomeric purity, exceeding 95% for each fraction, was determined before and after deprotection using two independent methods. The absolute configuration was rationally assigned by application of enantiomerically pure phosphinic acid substrates in the synthetic procedure and correlation with biological activity of the products. Substantial differences in inhibition of leucine aminopeptidase by the individual isomers revealed novel insights into potency of the recently developed and remarkably effective compound. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.107