(2S,3S)-3-[(S)-(Dimethyl-phenyl-silanyl)-p-tolyl-methyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester | 138331-59-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-3-[(S)-(Dimethyl-phenyl-silanyl)-p-tolyl-methyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester
• CAS: 138331-59-6
• 化学式: C₂₈H₃₁NO₄Si
• 分子量: 473.644
• InChiKey: MOTIUGFNDWIMQV-UODIDJSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  对甲基肉桂酸甲酯 、 dimethyl(phenyl)silyllithium 、 (4-methoxyphenyl-benzylidene)-carbamic acid methyl ester 生成 (2R,3S)-3-[(S)-(Dimethyl-phenyl-silanyl)-p-tolyl-methyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methyl ester 、 (2S,3S)-3-[(S)-(Dimethyl-phenyl-silanyl)-p-tolyl-methyl]-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

• A highly stereoselective formal synthesis of (±)-thienamycin through organocopper enolate–iminoester condensation
  作者：Claudio Palomo、Jesus M. Aizpurua、Raquel Urchegui

  DOI：10.1039/c39900001390

  日期：——

  crotonate and enolate trapping by methyl 4-methoxyphenyliminoacetate produced a high yield of (1′S*,3R*,4S)-3-[1-(dimethylphenylsilyl)ethyl]-4-methoxycarbonyl-1-(4-methoxyphenyl)azetidin-2-one as a (±)-thienamycin building block.

  将弗莱明甲硅烷基杯酸酯试剂共轭添加到巴豆酸甲酯中，并通过4-甲氧基苯基亚氨基乙酸甲酯捕获烯醇化物，得到高产率的（1 'S *，3 R *，4 S）-3- [1-（二甲基苯基甲硅烷基）乙基] -4 -甲氧基羰基-1-（4-甲氧基苯基）氮杂环丁烷-2-one作为（±）-噻吩霉素的构建基块。