(-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((4S,5S)-3-((4-nitrophenyl)sulfonyl)-2-oxo-4-vinyloxazolidin-5-yl)-4-oxoazetidin-3-yl)carbamate | 1237479-08-1

• 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: (-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((4S,5S)-3-((4-nitrophenyl)sulfonyl)-2-oxo-4-vinyloxazolidin-5-yl)-4-oxoazetidin-3-yl)carbamate
• 英文别名: tert-butyl N-[(2R,3R)-1-[tert-butyl(dimethyl)silyl]-2-[(4S,5S)-4-ethenyl-3-(4-nitrophenyl)sulfonyl-2-oxo-1,3-oxazolidin-5-yl]-4-oxoazetidin-3-yl]carbamate
• CAS: 1237479-08-1
• 化学式: C₂₅H₃₆N₄O₉SSi
• 分子量: 596.734
• InChiKey: ZMCYFKSFVOEWRD-MTQWCTHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  177
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((4S,5S)-3-((4-nitrophenyl)sulfonyl)-2-oxo-4-vinyloxazolidin-5-yl)-4-oxoazetidin-3-yl)carbamate 在 potassium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以93%的产率得到(-)-tert-butyl ((3R,4R)-1-(tert-butyldimethylsilyl)-2-oxo-4-((4S,5R)-2-oxo-4-vinyloxazolidin-5-yl)azetidin-3-yl)carbamate
  参考文献：
  名称：

  Diversification of a β-lactam pharmacophore via allylic C–H amination: accelerating effect of Lewis acid co-catalyst

  摘要：

  This report describes the use of Pd(II)/bis-sulfoxide 1 catalyzed intra- and intermolecular allylic C-H amination reactions to rapidly diversify structures containing a sensitive beta-lactam core similar to that found in the monobactam antibiotic Aztreonam. Pharmacologically interesting oxazolidinone, oxazinanone, and linear amine motifs are rapidly installed with predictable and high selectivities under conditions that use limiting amounts of substrate. Additionally, we demonstrate for the first time that intramolecular C-H amination processes may be accelerated using catalytic amounts of a Lewis acid co-catalyst [Cr(III)(salen)Cl 2]. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.064
• 作为产物：
  描述：

  (-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((R)-1-((((4-nitrophenyl)sulfonyl)carbamoyl)oxy)but-3-en-1-yl)-4-oxoazetidin-3-yl)carbamate 在 (R,R)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminochromium(III) chloride 、 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 1,2-二苯亚磺酰基乙烷 、 氧气 、 苯基-P-苯醌 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以76%的产率得到(-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((4S,5S)-3-((4-nitrophenyl)sulfonyl)-2-oxo-4-vinyloxazolidin-5-yl)-4-oxoazetidin-3-yl)carbamate
  参考文献：
  名称：

  Diversification of a β-lactam pharmacophore via allylic C–H amination: accelerating effect of Lewis acid co-catalyst

  摘要：

  This report describes the use of Pd(II)/bis-sulfoxide 1 catalyzed intra- and intermolecular allylic C-H amination reactions to rapidly diversify structures containing a sensitive beta-lactam core similar to that found in the monobactam antibiotic Aztreonam. Pharmacologically interesting oxazolidinone, oxazinanone, and linear amine motifs are rapidly installed with predictable and high selectivities under conditions that use limiting amounts of substrate. Additionally, we demonstrate for the first time that intramolecular C-H amination processes may be accelerated using catalytic amounts of a Lewis acid co-catalyst [Cr(III)(salen)Cl 2]. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.064

文献信息

• Diversification of a β-lactam pharmacophore via allylic C–H amination: accelerating effect of Lewis acid co-catalyst
  作者：Xiangbing (Ben) Qi、Grant T. Rice、Manjinder S. Lall、Mark S. Plummer、M. Christina White

  DOI：10.1016/j.tet.2010.04.064

  日期：2010.6

  This report describes the use of Pd(II)/bis-sulfoxide 1 catalyzed intra- and intermolecular allylic C-H amination reactions to rapidly diversify structures containing a sensitive beta-lactam core similar to that found in the monobactam antibiotic Aztreonam. Pharmacologically interesting oxazolidinone, oxazinanone, and linear amine motifs are rapidly installed with predictable and high selectivities under conditions that use limiting amounts of substrate. Additionally, we demonstrate for the first time that intramolecular C-H amination processes may be accelerated using catalytic amounts of a Lewis acid co-catalyst [Cr(III)(salen)Cl 2]. (C) 2010 Elsevier Ltd. All rights reserved.