Pentanedioic acid mono-[(2S,5R)-1-benzyloxycarbonyl-5-(dimethoxy-phosphorylmethyl)-pyrrolidin-2-ylmethyl] ester | 172885-72-2

• 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: Pentanedioic acid mono-[(2S,5R)-1-benzyloxycarbonyl-5-(dimethoxy-phosphorylmethyl)-pyrrolidin-2-ylmethyl] ester
• 英文别名: 5-[[(2S,5R)-5-(dimethoxyphosphorylmethyl)-1-phenylmethoxycarbonylpyrrolidin-2-yl]methoxy]-5-oxopentanoic acid
• CAS: 172885-72-2
• 化学式: C₂₁H₃₀NO₉P
• 分子量: 471.444
• InChiKey: QBBHGBVTVQWZQI-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Pentanedioic acid mono-[(2S,5R)-1-benzyloxycarbonyl-5-(dimethoxy-phosphorylmethyl)-pyrrolidin-2-ylmethyl] ester 在 叔丁胺 作用下， 反应 168.0h， 以47%的产率得到Pentanedioic acid mono-[(2S,5R)-1-benzyloxycarbonyl-5-(hydroxy-methoxy-phosphorylmethyl)-pyrrolidin-2-ylmethyl] 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：

  [(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidin-2-yl]-methanol 在 草酰氯 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 167.33h， 生成 Pentanedioic acid mono-[(2S,5R)-1-benzyloxycarbonyl-5-(dimethoxy-phosphorylmethyl)-pyrrolidin-2-ylmethyl] 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

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.