methoxy-[[(2R,5S)-5-[[3-oxo-3-(2-trimethylsilylethoxy)propyl]carbamoyloxymethyl]-1-phenylmethoxycarbonylpyrrolidin-2-yl]methyl]phosphinic acid | 1026493-28-6

• 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: methoxy-[[(2R,5S)-5-[[3-oxo-3-(2-trimethylsilylethoxy)propyl]carbamoyloxymethyl]-1-phenylmethoxycarbonylpyrrolidin-2-yl]methyl]phosphinic acid
• CAS: 1026493-28-6
• 化学式: C₂₄H₃₉N₂O₉PSi
• 分子量: 558.641
• InChiKey: UOVJPHVGKVVDAT-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methoxy-[[(2R,5S)-5-[[3-oxo-3-(2-trimethylsilylethoxy)propyl]carbamoyloxymethyl]-1-phenylmethoxycarbonylpyrrolidin-2-yl]methyl]phosphinic acid 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (2S,5R)-2-(2-Carboxy-ethylcarbamoyloxymethyl)-5-(hydroxy-methoxy-phosphorylmethyl)-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Catalytic Antibodies in Synthesis:  Design and Synthesis of a Hapten for Application to the Preparation of a Scalemic Pyrrolidine Ring Synthon for Ptilomycalin A

  摘要：

  A catalytic antibody-based approach toward the synthesis of an optically active pyrrolidine ring synthon potentially useful for ptilomycalin A is described. Enantiomerically pure hapten 37 was designed and constructed with the eventual goal of generating antibodies for the enantioselective partial hydrolysis of a meso diester such as 44 into a monoacid 45. This transition state analog possesses a phosphonate group containing the requisite oxyanionic character of the tetrahedral intermediate for ester hydrolysis. A newly developed carbamate-based linker, which was found to be much more hydrolytically stable than the commonly used glutarate ester, was developed for coupling of the hapten to a carrier protein.

  DOI：

  10.1021/jo951469t
• 作为产物：
  描述：

  丁二酸单(2-三甲基硅乙基)醚 在 二苯基磷酸 、 叔丁胺 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 192.0h， 生成 methoxy-[[(2R,5S)-5-[[3-oxo-3-(2-trimethylsilylethoxy)propyl]carbamoyloxymethyl]-1-phenylmethoxycarbonylpyrrolidin-2-yl]methyl]phosphinic acid
  参考文献：
  名称：

  Catalytic Antibodies in Synthesis:  Design and Synthesis of a Hapten for Application to the Preparation of a Scalemic Pyrrolidine Ring Synthon for Ptilomycalin A

  摘要：

  A catalytic antibody-based approach toward the synthesis of an optically active pyrrolidine ring synthon potentially useful for ptilomycalin A is described. Enantiomerically pure hapten 37 was designed and constructed with the eventual goal of generating antibodies for the enantioselective partial hydrolysis of a meso diester such as 44 into a monoacid 45. This transition state analog possesses a phosphonate group containing the requisite oxyanionic character of the tetrahedral intermediate for ester hydrolysis. A newly developed carbamate-based linker, which was found to be much more hydrolytically stable than the commonly used glutarate ester, was developed for coupling of the hapten to a carrier protein.

  DOI：

  10.1021/jo951469t

文献信息

• Catalytic Antibodies in Synthesis:  Design and Synthesis of a Hapten for Application to the Preparation of a Scalemic Pyrrolidine Ring Synthon for Ptilomycalin A
  作者：Glen T. Anderson、Michael D. Alexander、Scott D. Taylor、David B. Smithrud、Stephen J. Benkovic、Steven M. Weinreb

  DOI：10.1021/jo951469t

  日期：1996.1.1

  A catalytic antibody-based approach toward the synthesis of an optically active pyrrolidine ring synthon potentially useful for ptilomycalin A is described. Enantiomerically pure hapten 37 was designed and constructed with the eventual goal of generating antibodies for the enantioselective partial hydrolysis of a meso diester such as 44 into a monoacid 45. This transition state analog possesses a phosphonate group containing the requisite oxyanionic character of the tetrahedral intermediate for ester hydrolysis. A newly developed carbamate-based linker, which was found to be much more hydrolytically stable than the commonly used glutarate ester, was developed for coupling of the hapten to a carrier protein.