(2S-trans)-1-[bis(1-methylethoxy)phosphinyl]tetrahydro-4-hydroxy-2H-pyrrole-2-carboxylic acid diphenylphosphinyl ester | 266337-23-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S-trans)-1-[bis(1-methylethoxy)phosphinyl]tetrahydro-4-hydroxy-2H-pyrrole-2-carboxylic acid diphenylphosphinyl ester
• 英文别名: diphenylphosphoryl (2S,4R)-1-di(propan-2-yloxy)phosphoryl-4-hydroxypyrrolidine-2-carboxylate
• CAS: 266337-23-9
• 化学式: C₂₃H₃₁NO₇P₂
• 分子量: 495.449
• InChiKey: IHYJXIUERLZNQZ-KNQAVFIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S-trans)-1-[bis(1-methylethoxy)phosphinyl]tetrahydro-4-hydroxy-2H-pyrrole-2-carboxylic acid diphenylphosphinyl ester 在 吡啶 、 sodium sulfide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.61h， 生成 (1S)-(3-oxo-2-thio-5-azabicyclo[2.2.1]hept-5-yl)phosphonic acid bis(1-methylethyl) ester
  参考文献：
  名称：

  Efficient One-Pot Synthesis of the 2-Aminocarbonylpyrrolidin-4-ylthio-Containing Side Chain of the New Broad-Spectrum Carbapenem Antibiotic Ertapenem

  摘要：

  An efficient synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio containing side chain of ertapenem (MK-0826) is described. Starting material N-(O,O-diisopropyl phosphoryl)-trans-4-hydroxy-L-proline is converted in a one-pot process to (2S)-cis-3- [[(4-mercapto-2-pyrrolidinyl)carbonyl] amino] benzoic acid monohydrochloride in 70-75% overall yield via a series of six reactions. The development of each of these reactions and the isolation of the product is discussed in detail.

  DOI：

  10.1021/jo011170c
• 作为产物：
  描述：

  (2S,4r)-1-(二异丙氧基膦)-4-羟基吡咯烷-2-羧酸 、 二苯基次膦酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以56%的产率得到(2S-trans)-1-[bis(1-methylethoxy)phosphinyl]tetrahydro-4-hydroxy-2H-pyrrole-2-carboxylic acid diphenylphosphinyl ester
  参考文献：
  名称：

  Efficient One-Pot Synthesis of the 2-Aminocarbonylpyrrolidin-4-ylthio-Containing Side Chain of the New Broad-Spectrum Carbapenem Antibiotic Ertapenem

  摘要：

  An efficient synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio containing side chain of ertapenem (MK-0826) is described. Starting material N-(O,O-diisopropyl phosphoryl)-trans-4-hydroxy-L-proline is converted in a one-pot process to (2S)-cis-3- [[(4-mercapto-2-pyrrolidinyl)carbonyl] amino] benzoic acid monohydrochloride in 70-75% overall yield via a series of six reactions. The development of each of these reactions and the isolation of the product is discussed in detail.

  DOI：

  10.1021/jo011170c

文献信息

• Efficient One-Pot Synthesis of the 2-Aminocarbonylpyrrolidin-4-ylthio-Containing Side Chain of the New Broad-Spectrum Carbapenem Antibiotic Ertapenem
  作者：Karel M. J. Brands、Ronald B. Jobson、Karen M. Conrad、J. Michael Williams、Brenda Pipik、Mark Cameron、Antony J. Davies、Peter G. Houghton、Michael S. Ashwood、Ian F. Cottrell、Robert A. Reamer、Derek J. Kennedy、Ulf-H. Dolling、Paul J. Reider

  DOI：10.1021/jo011170c

  日期：2002.7.1

  An efficient synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio containing side chain of ertapenem (MK-0826) is described. Starting material N-(O,O-diisopropyl phosphoryl)-trans-4-hydroxy-L-proline is converted in a one-pot process to (2S)-cis-3- [[(4-mercapto-2-pyrrolidinyl)carbonyl] amino] benzoic acid monohydrochloride in 70-75% overall yield via a series of six reactions. The development of each of these reactions and the isolation of the product is discussed in detail.