(3R,4S)-3-ethyl-4-<(S)-1-<(tert-butyldimethylsilyl)oxy>-ethyl>-2-azetidinone | 116078-97-8

• 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-<(tert-butyldimethylsilyl)oxy>-ethyl>-2-azetidinone
• 英文别名: (3R,4S)-3-ethyl-4-{(S)-1-[(tert-butyldimethylsilyl)oxy]-ethyl}-2-azetidinone；(3R,4S)-4-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-3-ethylazetidin-2-one
• CAS: 116078-97-8
• 化学式: C₁₃H₂₇NO₂Si
• 分子量: 257.448
• InChiKey: FONBICINWRYSSF-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (S)-2-(叔丁基-二甲基-锡氧基)-丙醛 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (3R,4S)-3-ethyl-4-<(S)-1-<(tert-butyldimethylsilyl)oxy>-ethyl>-2-azetidinone
  参考文献：
  名称：

  Stereoselective synthesis of .beta.-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines

  摘要：

  A mild and versatile one-pot synthesis of beta-lactams has been performed by condensation of the easily generated titantium enolates of 2-pyridyl thioesters with imines employing chiral reaction partners. Both imines obtained from enantiomerically pure alkoxy aldehydes and the enolate derived from 3-hydroxybutyrate showed high diastereofacial preferences, efficiently transferring the stereochemical information to the stereocenters of the azetidinone ring. Advanced precursors of (+)-PS-5, (+)-PS-6, thienamycin, and 1-beta-methylthienamycin were prepared to illustrate the potential of this method. A H-1-NMR study of the enolization process and a tentative rationalization of the stereochemical results are presented.

  DOI：

  10.1021/jo00041a019

文献信息

• Preparation of chiral 3-unsubstituted β-lactams from 3-hydroxy β-lactams by using the alkoxyketene-imine cycloaddition reaction as an approach to the azetidinone ring: A formal synthesis of the carbapenem antibiotic (+)-PS-5.
  作者：Claudio Palomo、Fernando P. Cossío、Jesús M. Ontoria、José M. Odriozola

  DOI：10.1016/0040-4039(91)80701-7

  日期：1991.6

  Formation of chiral 3-hydroxy β-lactams from the alkoxyketene-imine cycloaddition reaction followed by deoxygenation under Barton's conditions provided a simple roam to optically active 3-unsubstituted β-lactams.

  由烷氧基乙烯酮-亚胺环加成反应形成手性3-羟基β-内酰胺，然后在巴顿条件下进行脱氧，为光学活性的3-未取代的β-内酰胺提供了简单的漫游条件。
• .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：——