(R)-1-(2,4-Dimethoxy-benzyl)-4-oxo-3-[3-(2,2,2-trifluoro-acetylamino)-propyl]-azetidine-2,2-dicarboxylic acid dimethyl ester | 439089-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (R)-1-(2,4-Dimethoxy-benzyl)-4-oxo-3-[3-(2,2,2-trifluoro-acetylamino)-propyl]-azetidine-2,2-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl (3R)-1-[(2,4-dimethoxyphenyl)methyl]-4-oxo-3-[3-[(2,2,2-trifluoroacetyl)amino]propyl]azetidine-2,2-dicarboxylate
• CAS: 439089-67-5
• 化学式: C₂₁H₂₅F₃N₂O₈
• 分子量: 490.433
• InChiKey: OGWBOESYJKSNQP-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (R)-1-(2,4-Dimethoxy-benzyl)-4-oxo-3-[3-(2,2,2-trifluoro-acetylamino)-propyl]-azetidine-2,2-dicarboxylic acid dimethyl ester 在 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (2S,3R)-1-(2,4-Dimethoxy-benzyl)-4-oxo-3-[3-(2,2,2-trifluoro-acetylamino)-propyl]-azetidine-2-carboxylic acid methyl ester 、 (2R,3R)-1-(2,4-Dimethoxy-benzyl)-4-oxo-3-[3-(2,2,2-trifluoro-acetylamino)-propyl]-azetidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  A Stereoselective Synthesis of BMS-262084, an Azetidinone-Based Tryptase Inhibitor

  摘要：

  A highly stereoselective synthesis of the novel tryptase inhibitor BMS-262084 was developed. Key to this synthesis was the discovery and development of a highly diastereoselective demethoxycarbonylation of diester 12 to form the trans-azetidinone 13. BMS-262084 was prepared in 10 steps from D-ornithine in 30% overall yield.

  DOI：

  10.1021/jo010757o
• 作为产物：
  描述：

  2,4-二甲氧基苯甲醛 在 palladium on activated charcoal dipotassium hydrogenphosphate 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (R)-1-(2,4-Dimethoxy-benzyl)-4-oxo-3-[3-(2,2,2-trifluoro-acetylamino)-propyl]-azetidine-2,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  A Stereoselective Synthesis of BMS-262084, an Azetidinone-Based Tryptase Inhibitor

  摘要：

  A highly stereoselective synthesis of the novel tryptase inhibitor BMS-262084 was developed. Key to this synthesis was the discovery and development of a highly diastereoselective demethoxycarbonylation of diester 12 to form the trans-azetidinone 13. BMS-262084 was prepared in 10 steps from D-ornithine in 30% overall yield.

  DOI：

  10.1021/jo010757o

文献信息

• A Stereoselective Synthesis of BMS-262084, an Azetidinone-Based Tryptase Inhibitor
  作者：Xinhua Qian、Bin Zheng、Brian Burke、Manohar T. Saindane、David R. Kronenthal

  DOI：10.1021/jo010757o

  日期：2002.5.1

  A highly stereoselective synthesis of the novel tryptase inhibitor BMS-262084 was developed. Key to this synthesis was the discovery and development of a highly diastereoselective demethoxycarbonylation of diester 12 to form the trans-azetidinone 13. BMS-262084 was prepared in 10 steps from D-ornithine in 30% overall yield.