Methyl 2(S*)-(benzoylamino)-4-hydroxy-3(R*)-(methoxycarbonyl)-4-methylpentanoate | 138235-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 2(S*)-(benzoylamino)-4-hydroxy-3(R*)-(methoxycarbonyl)-4-methylpentanoate
• 英文别名: dimethyl (2S,3S)-2-benzamido-3-(2-hydroxypropan-2-yl)butanedioate
• CAS: 138235-21-9
• 化学式: C₁₆H₂₁NO₆
• 分子量: 323.346
• InChiKey: BNHRKEJWYYZEOQ-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  trans,anti-3-<1'-(Dimethylphenylsilyl)-2'-propyl>-4-(methoxycarbonyl)azetidin-2-one 在 过氧乙酸 、 四氟硼酸-二乙醚络合物 、 三甲基氯硅烷 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 12.0h， 生成 Methyl 2(S*)-(benzoylamino)-4-hydroxy-3(R*)-(methoxycarbonyl)-4-methylpentanoate
  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

• Formation of 3-[1'-(dimethylphenylsilyl)ethyl]azetidin-2-ones: stereocontrolled formal approach to (.+-.)-thienamycin and (.+-.)-.beta.-(hydroxyalkyl)aspartic acid derivatives
  作者：Claudio Palomo、Jesus M. Aizpurua、Raquel Urchegui、Miren Iturburu

  DOI：10.1021/jo00031a044

  日期：1992.2

  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.