Toluene-4-sulfonic acid (S)-2-((2S,3S)-2-acetyl-3-ethyl-4-oxo-azetidin-1-yl)-2-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester | 188989-42-6

• 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: Toluene-4-sulfonic acid (S)-2-((2S,3S)-2-acetyl-3-ethyl-4-oxo-azetidin-1-yl)-2-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester
• 英文别名: [(2S)-2-[(2S,3S)-2-acetyl-3-ethyl-4-oxoazetidin-1-yl]-2-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl] 4-methylbenzenesulfonate
• CAS: 188989-42-6
• 化学式: C₂₆H₃₇NO₉S
• 分子量: 539.647
• InChiKey: NOZNHDHNRIAOPH-ZFPSYYEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  苯基氯化硒 、 Toluene-4-sulfonic acid (S)-2-((2S,3S)-2-acetyl-3-ethyl-4-oxo-azetidin-1-yl)-2-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以20%的产率得到Toluene-4-sulfonic acid (S)-2-[(3S,4S)-3-ethyl-2-oxo-4-(2-phenylselanyl-acetyl)-azetidin-1-yl]-2-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Unnatural 6α-trans-2-Oxaisochephams and Δ¹⁽⁶⁾-2-Oxaisocephems

  摘要：

  Several 4β-acetyl-3β-ethyl-N-substituted 2-azetidinones have been synthesized by the Staudinger reaction with D-glucosamine as chiral auxiliary. Attempts to perform an intramolecular cyclisation between the C-4 and N-substituents under ionic conditions at low temperature failed, but a room temperature (thermodynamic control) the bicyclic β-lactams 4-(1,2;3,4-di-O-isopropylidene-1,2,3,4-arabino-tetrahydroxybutyl)-7β-ethyl-1-methylene-6α-2-oxaisocepham and the Δ1(6) isomer were obtained.

  DOI：

  10.1055/s-1997-5786
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (S)-2-[(2S,3S)-3-ethyl-2-((E)-1-methyl-2-phenyl-vinyl)-4-oxo-azetidin-1-yl]-2-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 Toluene-4-sulfonic acid (S)-2-((2S,3S)-2-acetyl-3-ethyl-4-oxo-azetidin-1-yl)-2-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Unnatural 6α-trans-2-Oxaisochephams and Δ¹⁽⁶⁾-2-Oxaisocephems

  摘要：

  Several 4β-acetyl-3β-ethyl-N-substituted 2-azetidinones have been synthesized by the Staudinger reaction with D-glucosamine as chiral auxiliary. Attempts to perform an intramolecular cyclisation between the C-4 and N-substituents under ionic conditions at low temperature failed, but a room temperature (thermodynamic control) the bicyclic β-lactams 4-(1,2;3,4-di-O-isopropylidene-1,2,3,4-arabino-tetrahydroxybutyl)-7β-ethyl-1-methylene-6α-2-oxaisocepham and the Δ1(6) isomer were obtained.

  DOI：

  10.1055/s-1997-5786