(5R,6R)-benzhydryl 3-<(2-acetamidoethyl)thio>-6-isopropyl-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate | 135560-72-4

• 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: (5R,6R)-benzhydryl 3-<(2-acetamidoethyl)thio>-6-isopropyl-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
• 英文别名: benzhydryl (5R,6R)-3-(2-acetamidoethylsulfanyl)-7-oxo-6-propan-2-yl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 135560-72-4
• 化学式: C₂₇H₃₀N₂O₄S
• 分子量: 478.612
• InChiKey: CHVFXKOFDSXRBA-FYYLOGMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5R,6R)-benzhydryl 3-<(2-acetamidoethyl)thio>-6-isopropyl-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate 在 三氯化铝 、 苯甲醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以40%的产率得到(5R,6R)-sodium 3-<(2-acetamidoethyl)thio>-6-isopropyl-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
  参考文献：
  名称：

  .beta.-Lactams from ester enolates and silylimines: enantioselective synthesis of the trans-carbapenem antibiotics (+)-PS-5 and (+)-PS-6

  摘要：

  A new synthetic route to the antibiotics (+)-PS-5 and (+)-PS-6 is described. The preparation involves a fully stereocontrolled reaction between the enantiomerically pure N-trimethylsilylimine of lactic or mandelic aldehyde and the lithium enolate of the tert-butyl butanoate or tert-butyl isovalerate, respectively. Conversion of the azetidinones obtained to 4-acetoxy derivatives via oxidative cleavage of the hydroxyethyl or hydroxybenzyl side chain and introduction of the necessary appendage in the position 4 of the azetidinone ring, followed by assemblage of the bicyclic ring system, afforded the natural trans-carbapenems (+)-PS-5 and (+)-PS-6.

  DOI：

  10.1021/jo00021a007
• 作为产物：
  描述：

  (2R,5R,6R)-benzhydryl 6-isopropyl-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 19.0h， 生成 (5R,6R)-benzhydryl 3-<(2-acetamidoethyl)thio>-6-isopropyl-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
  参考文献：
  名称：

  .beta.-Lactams from ester enolates and silylimines: enantioselective synthesis of the trans-carbapenem antibiotics (+)-PS-5 and (+)-PS-6

  摘要：

  A new synthetic route to the antibiotics (+)-PS-5 and (+)-PS-6 is described. The preparation involves a fully stereocontrolled reaction between the enantiomerically pure N-trimethylsilylimine of lactic or mandelic aldehyde and the lithium enolate of the tert-butyl butanoate or tert-butyl isovalerate, respectively. Conversion of the azetidinones obtained to 4-acetoxy derivatives via oxidative cleavage of the hydroxyethyl or hydroxybenzyl side chain and introduction of the necessary appendage in the position 4 of the azetidinone ring, followed by assemblage of the bicyclic ring system, afforded the natural trans-carbapenems (+)-PS-5 and (+)-PS-6.

  DOI：

  10.1021/jo00021a007