(3R,4S)-3-ethyl-4-<(S)-1-hydroxyethyl>-2-azetidinone | 116078-98-9

• 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: (3R,4S)-3-ethyl-4-<(S)-1-hydroxyethyl>-2-azetidinone
• 英文别名: (3R,4S)-3-ethyl-4-[(1S)-1-hydroxyethyl]azetidin-2-one
• CAS: 116078-98-9
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: DZNQMOWRQTZUOB-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-ethyl-4-<(S)-1-hydroxyethyl>-2-azetidinone 以76%的产率得到
  参考文献：
  名称：

  CAINELLI, GIANFRANCO;PANUNZIO, MAURO;GIACOMINI, DARIA;MARTELLI, GIORGIO;S+, J. AMER. CHEM. SOC., 110,(1988) N 20, C. 6879-6880

  摘要：

  DOI：
• 作为产物：
  描述：

  (3R,4S)-3-ethyl-4-<(S)-1-<(tert-butyldimethylsilyl)oxy>-ethyl>-2-azetidinone 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以97%的产率得到(3R,4S)-3-ethyl-4-<(S)-1-hydroxyethyl>-2-azetidinone
  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

文献信息

• .beta.-Lactams from ester enolates and silylimines. Enantioselective synthesis of (+)-PS-5
  作者：Gianfranco. Cainelli、Mauro. Panunzio、Daria. Giacomini、Giorgio. Martelli、Giuseppe. Spunta

  DOI：10.1021/ja00228a044

  日期：1988.9
• CAINELLI, GIANFRANCO;PANUNZIO, MAURO;GIACOMINI, DARIA;MARTELLI, GIORGIO;S+, J. AMER. CHEM. SOC., 110,(1988) N 20, C. 6879-6880
  作者：CAINELLI, GIANFRANCO、PANUNZIO, MAURO、GIACOMINI, DARIA、MARTELLI, GIORGIO、S+

  DOI：——

  日期：——
• .beta.-Lactams from ester enolates and silylimines: enantioselective synthesis of the trans-carbapenem antibiotics (+)-PS-5 and (+)-PS-6
  作者：Patrizia Andreoli、Gianfranco Cainelli、Mauro Panunzio、Elisa Bandini、Giorgio Martelli、Giuseppe Spunta

  DOI：10.1021/jo00021a007

  日期：1991.10

  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.