(2S,3S)-3-[(S)-1-(Dimethyl-phenyl-silanyl)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester | 128571-95-9

• 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: (2S,3S)-3-[(S)-1-(Dimethyl-phenyl-silanyl)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester
• CAS: 128571-95-9
• 化学式: C₂₂H₂₇NO₄Si
• 分子量: 397.546
• InChiKey: BWPXACQNXITPCX-YSSFQJQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-[(S)-1-(Dimethyl-phenyl-silanyl)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester 在 四氟硼酸-二乙醚络合物 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2R,3R)-3-[(R)-1-(Fluoro-dimethyl-silanyl)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Formation of 3-[1'-(dimethylphenylsilyl)ethyl]azetidin-2-ones: stereocontrolled formal approach to (.+-.)-thienamycin and (.+-.)-.beta.-(hydroxyalkyl)aspartic acid derivatives

  摘要：

  Reaction between (+/-)-beta-(dimethylphenylsilyl)alkanoyl chlorides and imines of glyoxylic esters provided a route to (+/-)-cis-3-[1'-(dimethylphenylsilyl)ethyl]-4-alkoxycarbonyl beta-lactams, while addition of the Fleming's silylcuprate reagent to methyl crotonate and further enolate trapping by the above imines furnished the corresponding (+/-)-trans-3-[1'-(dimethylphenylsilyl)ethyl]-4-alkoxycarbonyl beta-lactams. These beta-lactams, upon appropriate chemical manipulations, provided a stereocontrolled route to (+/-)-thienamycin precursors and (+/-)-beta-(hydroxyalkyl)aspartic acid derivatives.

  DOI：

  10.1021/jo00031a044
• 作为产物：
  描述：

  (3RS)-3-dimethyl(phenyl)silylbutanoic acid 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 (2S,3S)-3-[(S)-1-(Dimethyl-phenyl-silanyl)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Formation of 3-[1'-(dimethylphenylsilyl)ethyl]azetidin-2-ones: stereocontrolled formal approach to (.+-.)-thienamycin and (.+-.)-.beta.-(hydroxyalkyl)aspartic acid derivatives

  摘要：

  Reaction between (+/-)-beta-(dimethylphenylsilyl)alkanoyl chlorides and imines of glyoxylic esters provided a route to (+/-)-cis-3-[1'-(dimethylphenylsilyl)ethyl]-4-alkoxycarbonyl beta-lactams, while addition of the Fleming's silylcuprate reagent to methyl crotonate and further enolate trapping by the above imines furnished the corresponding (+/-)-trans-3-[1'-(dimethylphenylsilyl)ethyl]-4-alkoxycarbonyl beta-lactams. These beta-lactams, upon appropriate chemical manipulations, provided a stereocontrolled route to (+/-)-thienamycin precursors and (+/-)-beta-(hydroxyalkyl)aspartic acid derivatives.

  DOI：

  10.1021/jo00031a044

文献信息

• Preparation of 3-alkyl .beta.-lactams via the ketene imine cycloaddition reaction using .alpha.-(phenylthio)alkanoyl halides as starting materials: application to the synthesis of (.+-.)-carbapenem building blocks and related compounds
  作者：Claudio Palomo、Fernando P. Cossio、Jose M. Odiozola、Mikel Oiarbide、Jesus M. Ontoria

  DOI：10.1021/jo00014a017

  日期：1991.7

  Preparation of appropriately substituted 3-alkyl beta-lactams via the ketene (or equivalent)-imine cycloaddition reaction is described. The dehydrochlorination reaction of alpha-(phenylthio)alkanoyl chlorides with triethylamine in the presence of imines derived from cinnamaldehydes and p-anisidine produced a high-yield formation of alpha-phenylthio beta-lactams, which upon desulfuration furnished a variety of 3-alkyl beta-lactams in a highly stereoselective fashion. In contrast, reaction between alpha-haloalkanoyl chlorides and cinnamylideneamines in the presence of triethylamine furnished the corresponding [4 + 2] cycloadducts as main products. Preparation of highly functionalized alpha-alkylidene beta-lactams through thermal decomposition of the corresponding beta-lactam sulfoxides or by cycloaddition of alpha,beta-unsaturated acid chlorides to imino esters in the presence of triethylamine is also described. Addition of Flemming's silylcuprate reagent to alpha-alkylidene beta-lactams furnished the corresponding 3-(1'-(dimethylphenylsilyl(ethyl) beta-lactams as (+/-)-thienamycin intermediates.