(3S,4R)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-4-[(1R,2S)-2-tert-butyldimethylsilyloxy-5-hydroxy-1-methylpent-3-ynyl]-2-azetidinone | 622410-54-2

• 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: (3S,4R)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-4-[(1R,2S)-2-tert-butyldimethylsilyloxy-5-hydroxy-1-methylpent-3-ynyl]-2-azetidinone
• CAS: 622410-54-2
• 化学式: C₂₃H₄₅NO₄Si₂
• 分子量: 455.786
• InChiKey: LAMUPEVNBVUSEF-OMQSBVIBSA-N

物化性质

• 沸点：
  507.8±30.0 °C(Predicted)
• 密度：
  0.981±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  67.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-4-[(1R,2S)-2-tert-butyldimethylsilyloxy-5-hydroxy-1-methylpent-3-ynyl]-2-azetidinone 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 吡啶 、 caesium carbonate 、 三(邻甲基苯基)磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 11.0h， 生成 (1R,2S,5R,6S)-3-[(E)-2-benzoyloxyethylidene]-2-tert-butyldimethylsilyloxy-6-[(R)-1-tert-butyldimethylsilyloxyethyl]-1-methyl-carbapenam
  参考文献：
  名称：

  Novel Synthesis of Carbapenam by Intramolecular Attack of Lactam Nitrogen toward η¹-Allenyl and η³-Propargylpalladium Complex

  摘要：

  When a THF solution of beta-lactam having propargyl phosphate was warmed in the presence of 5 mol % of Pd-2(dba)(3).CHCl3, 20 mol % of a bidentate ligand, and sodium acetate (1.5 equiv) at 40 degreesC for 22 h, carbapenam was produced in high yield. In this reaction, the lactam nitrogen attacked the central carbon of a eta(3)-propargylpalladium complex, which was formed from propargyl phosphate and Pd(0).

  DOI：

  10.1021/jo030123c
• 作为产物：
  描述：

  2-Azetidinone,3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-4-[(1R,2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-methyl-3-butynyl]-, (3S,4R)- 在 potassium fluoride 、 正丁基锂 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 (3S,4R)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-4-[(1R,2S)-2-tert-butyldimethylsilyloxy-5-hydroxy-1-methylpent-3-ynyl]-2-azetidinone
  参考文献：
  名称：

  Novel Synthesis of Carbapenam by Intramolecular Attack of Lactam Nitrogen toward η¹-Allenyl and η³-Propargylpalladium Complex

  摘要：

  When a THF solution of beta-lactam having propargyl phosphate was warmed in the presence of 5 mol % of Pd-2(dba)(3).CHCl3, 20 mol % of a bidentate ligand, and sodium acetate (1.5 equiv) at 40 degreesC for 22 h, carbapenam was produced in high yield. In this reaction, the lactam nitrogen attacked the central carbon of a eta(3)-propargylpalladium complex, which was formed from propargyl phosphate and Pd(0).

  DOI：

  10.1021/jo030123c