(E)-4-(N-((benzyloxy)carbonyl)-4-methylphenylsulfonamido)-1-((2R,3R)-3-((tert-butoxycarbonyl)amino)-1-(tert-butyldimethylsilyl)-4-oxoazetidin-2-yl)but-2-en-1-yl acetate | 1237479-13-8

• 英文名称: (E)-4-(N-((benzyloxy)carbonyl)-4-methylphenylsulfonamido)-1-((2R,3R)-3-((tert-butoxycarbonyl)amino)-1-(tert-butyldimethylsilyl)-4-oxoazetidin-2-yl)but-2-en-1-yl acetate
• 英文别名: [(E)-1-[(2R,3R)-1-[tert-butyl(dimethyl)silyl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxoazetidin-2-yl]-4-[(4-methylphenyl)sulfonyl-phenylmethoxycarbonylamino]but-2-enyl] acetate
• CAS: 1237479-13-8
• 化学式: C₃₅H₄₉N₃O₉SSi
• 分子量: 715.94
• InChiKey: ZXYGEQYVKJAGLY-YRZVKBQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  157
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (E)-4-(N-((benzyloxy)carbonyl)-4-methylphenylsulfonamido)-1-((2R,3R)-3-((tert-butoxycarbonyl)amino)-1-(tert-butyldimethylsilyl)-4-oxoazetidin-2-yl)but-2-en-1-yl acetate 在 萘 、 sodium 、 氯化铵 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.58h， 以84%的产率得到(E)-4-(((benzyloxy)carbonyl)amino)-1-((2R,3R)-3-((tert-butoxycarbonyl)amino)-1-(tert-butyldimethylsilyl)-4-oxoazetidin-2-yl)but-2-en-1-yl acetate
  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：

  1-((2R,3R)-3-((tert-butoxycarbonyl)amino)-1-(tert-butyldimethylsilyl)-4-oxoazetidin-2-yl)but-3-en-1-yl acetate 、 benzyl N-(4-methylbenzenesulfonyl)carbamate 在 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 氧气 、 N,N-二异丙基乙胺 、 对苯醌 作用下， 以 甲基叔丁基醚 为溶剂， 反应 72.0h， 以55%的产率得到(E)-4-(N-((benzyloxy)carbonyl)-4-methylphenylsulfonamido)-1-((2R,3R)-3-((tert-butoxycarbonyl)amino)-1-(tert-butyldimethylsilyl)-4-oxoazetidin-2-yl)but-2-en-1-yl acetate
  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