diphenylphosphoryl (2S,4R)-1-di(propan-2-yloxy)phosphoryl-4-methylsulfonyloxypyrrolidine-2-carboxylate | 266337-24-0

• 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: diphenylphosphoryl (2S,4R)-1-di(propan-2-yloxy)phosphoryl-4-methylsulfonyloxypyrrolidine-2-carboxylate
• CAS: 266337-24-0
• 化学式: C₂₄H₃₃NO₉P₂S
• 分子量: 573.541
• InChiKey: XTLKHSCADFYJIH-OFNKIYASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  diphenylphosphoryl (2S,4R)-1-di(propan-2-yloxy)phosphoryl-4-methylsulfonyloxypyrrolidine-2-carboxylate 在 盐酸 、 sodium sulfide 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 52.11h， 生成 (2S)-cis-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride disulfide
  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 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 diphenylphosphoryl (2S,4R)-1-di(propan-2-yloxy)phosphoryl-4-methylsulfonyloxypyrrolidine-2-carboxylate
  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.