3-((1-(N-(benzyloxycarbonyl)amino)-2-phenylethyl)(methyloxy)phosphinyl)propanoic acid ethyl ester | 372983-75-0

• 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: 3-((1-(N-(benzyloxycarbonyl)amino)-2-phenylethyl)(methyloxy)phosphinyl)propanoic acid ethyl ester
• 英文别名: Ethyl 3-[methoxy-[2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoate
• CAS: 372983-75-0
• 化学式: C₂₂H₂₈NO₆P
• 分子量: 433.441
• InChiKey: LIUNUCCXBNYUMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-((1-(N-(benzyloxycarbonyl)amino)-2-phenylethyl)(methyloxy)phosphinyl)propanoic acid ethyl ester 在 劳森试剂 、 氢溴酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 21.0h， 生成 ethyl 3-[methoxy-[2-phenyl-1-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]ethyl]phosphinothioyl]propanoate
  参考文献：
  名称：

  Mapping the Pathway toward Thiophosphinic Pseudopeptides. Synthesis of Suitably Protected PG-Phe-Ψ[P(S)(OX)CH₂]-Gly-OY Analogues as Thiophosphinyl Dipeptide Isosters (TDI), a Comparative Study for Selective Deprotection and Further Elongation

  摘要：

  In the present study, we describe in detail the first synthesis of a new class of phosphorus compounds, thiophosphinyl pseudopeptides. We prepared several fully protected thiophosphinate pseudodipeptides of the general formula PG-Phe-Psi[P(S)(OX)CH2]-Gly-OY starting from the corresponding phosphinate pseudodipeptide using Lawesson's reagent. Selective deprotection, further elongation, and stability of these compounds were studied, and the results are disclosed. These compounds can be used as transition-state-mimicking inhibitors for several zinc metalloproteases.

  DOI：

  10.1021/jo401084v
• 作为产物：
  描述：

  (R,S)-3-((1'-(N-benzyloxycarbonylamino)-2'-phenylethyl)methyloxyphosphinyl)propanoic acid ethyl ester 、 三甲氧基磷 反应 10.0h， 以93%的产率得到3-((1-(N-(benzyloxycarbonyl)amino)-2-phenylethyl)(methyloxy)phosphinyl)propanoic acid ethyl ester
  参考文献：
  名称：

  Mapping the Pathway toward Thiophosphinic Pseudopeptides. Synthesis of Suitably Protected PG-Phe-Ψ[P(S)(OX)CH₂]-Gly-OY Analogues as Thiophosphinyl Dipeptide Isosters (TDI), a Comparative Study for Selective Deprotection and Further Elongation

  摘要：

  In the present study, we describe in detail the first synthesis of a new class of phosphorus compounds, thiophosphinyl pseudopeptides. We prepared several fully protected thiophosphinate pseudodipeptides of the general formula PG-Phe-Psi[P(S)(OX)CH2]-Gly-OY starting from the corresponding phosphinate pseudodipeptide using Lawesson's reagent. Selective deprotection, further elongation, and stability of these compounds were studied, and the results are disclosed. These compounds can be used as transition-state-mimicking inhibitors for several zinc metalloproteases.

  DOI：

  10.1021/jo401084v

文献信息

• Mapping the Pathway toward Thiophosphinic Pseudopeptides. Synthesis of Suitably Protected PG-Phe-Ψ[P(S)(OX)CH₂]-Gly-OY Analogues as Thiophosphinyl Dipeptide Isosters (TDI), a Comparative Study for Selective Deprotection and Further Elongation
  作者：Stamatia Vassiliou、Eirini Tzouma

  DOI：10.1021/jo401084v

  日期：2013.10.18

  In the present study, we describe in detail the first synthesis of a new class of phosphorus compounds, thiophosphinyl pseudopeptides. We prepared several fully protected thiophosphinate pseudodipeptides of the general formula PG-Phe-Psi[P(S)(OX)CH2]-Gly-OY starting from the corresponding phosphinate pseudodipeptide using Lawesson's reagent. Selective deprotection, further elongation, and stability of these compounds were studied, and the results are disclosed. These compounds can be used as transition-state-mimicking inhibitors for several zinc metalloproteases.