benzyl (2R,5S)-2-(dimethoxyphosphorylmethyl)-5-[[3-oxo-3-(2-trimethylsilylethoxy)propyl]carbamoyloxymethyl]pyrrolidine-1-carboxylate | 172885-74-4

• 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: benzyl (2R,5S)-2-(dimethoxyphosphorylmethyl)-5-[[3-oxo-3-(2-trimethylsilylethoxy)propyl]carbamoyloxymethyl]pyrrolidine-1-carboxylate
• CAS: 172885-74-4
• 化学式: C₂₅H₄₁N₂O₉PSi
• 分子量: 572.668
• InChiKey: LPMCACZONIRSNI-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  38
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl (2R,5S)-2-(dimethoxyphosphorylmethyl)-5-[[3-oxo-3-(2-trimethylsilylethoxy)propyl]carbamoyloxymethyl]pyrrolidine-1-carboxylate 在 叔丁胺 作用下， 反应 168.0h， 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
• 作为产物：
  描述：

  (2S,5R)-N-benzyl-5-methoxycarbonylproline 在 palladium dihydroxide 咪唑 、 sodium tetrahydroborate 、 草酰氯 、 偶氮二异丁腈 、 二苯基磷酸 、 氢气 、 三正丁基氢锡 、 氯甲酸乙酯 、 sodium hydride 、 二异丁基氢化铝 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~115.0 ℃ 、101.33 kPa 条件下， 反应 166.16h， 生成 benzyl (2R,5S)-2-(dimethoxyphosphorylmethyl)-5-[[3-oxo-3-(2-trimethylsilylethoxy)propyl]carbamoyloxymethyl]pyrrolidine-1-carboxylate
  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.