(2S,3R)-3-[3-[bis(phenylmethoxycarbonylamino)methylideneamino]propyl]-1-[(2,4-dimethoxyphenyl)methyl]-4-oxoazetidine-2-carboxylic acid | 439089-70-0

• 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: (2S,3R)-3-[3-[bis(phenylmethoxycarbonylamino)methylideneamino]propyl]-1-[(2,4-dimethoxyphenyl)methyl]-4-oxoazetidine-2-carboxylic acid
• CAS: 439089-70-0
• 化学式: C₃₃H₃₆N₄O₉
• 分子量: 632.67
• InChiKey: MCNLBUXQIHNZCW-IAPPQJPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  165
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-[3-[bis(phenylmethoxycarbonylamino)methylideneamino]propyl]-1-[(2,4-dimethoxyphenyl)methyl]-4-oxoazetidine-2-carboxylic acid 在 4-二甲氨基吡啶 、 dipotassium hydrogenphosphate 、 dipotassium peroxodisulfate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 9.3h， 生成 benzyl (2S,3R)-3-[3-[bis(phenylmethoxycarbonylamino)methylideneamino]propyl]-1-[4-(tert-butylcarbamoyl)piperazine-1-carbonyl]-4-oxoazetidine-2-carboxylate
  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：

  N,N'-双(苄氧羰基)-1H-吡唑-1-甲脒 、 (2S,3R)-3-(3-Amino-propyl)-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid; compound with acetic acid 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 6.33h， 生成 (2S,3R)-3-[3-[bis(phenylmethoxycarbonylamino)methylideneamino]propyl]-1-[(2,4-dimethoxyphenyl)methyl]-4-oxoazetidine-2-carboxylic acid
  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.