(1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-4-(2'-phenylethenyl)-2-azetidinone | 101905-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-4-(2'-phenylethenyl)-2-azetidinone
• 英文别名: (1'R,3S,4R)-3-{1'-[(tert-butyldimethylsilyl)oxy]ethyl}-4-(2'-phenylethenyl)-2-azetidinone
• CAS: 101905-27-5
• 化学式: C₁₉H₂₉NO₂Si
• 分子量: 331.53
• InChiKey: KQQHARCCDXMHOG-BZSKBRDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-4-(2'-phenylethenyl)-2-azetidinone 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 <3S-<3α(S^*),4β>>-3-(1-t-butyldimethylsilyloxyethyl)-4-hydroxymethyl-2-azetidinone
  参考文献：
  名称：

  从3-羟基丁酸酯完全合成硫霉素和相关β-内酰胺抗生素的手性中间体的立体和对映体控制的合成

  摘要：

  （1'的合成- [R，3小号，4小号） -和（1' - [R，3小号，4 - [R）-3-（1'-叔butyldimethylsilyoxyethyl）-4-羟甲基-2- azeidinone从乙基（小号）-3-羟基丁酸酯被报道。

  DOI：

  10.1039/c39850001433
• 作为产物：
  描述：

  (1'R,3S,4R)-3-[1'-((tert-butyldimethylsilyl)oxy)ethyl]-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以97%的产率得到(1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-4-(2'-phenylethenyl)-2-azetidinone
  参考文献：
  名称：

  从3-羟基丁酸酯完全合成硫霉素和相关β-内酰胺抗生素的手性中间体的立体和对映体控制的合成

  摘要：

  （1'的合成- [R，3小号，4小号） -和（1' - [R，3小号，4 - [R）-3-（1'-叔butyldimethylsilyoxyethyl）-4-羟甲基-2- azeidinone从乙基（小号）-3-羟基丁酸酯被报道。

  DOI：

  10.1039/c39850001433

文献信息

• Asymmetric synthesis of (1'R,3R,4R)-4-acetoxy-3-[1'-((tert-butyldimethylsilyl)oxy)ethyl]-2-azetidinone and other 3-(1'-hydroxyethyl)-2-azetidinones from (S)-(+)-ethyl 3-hydroxybutanoate: formal total synthesis of (+)-thienamycin
  作者：Gunda I. Georg、Joydeep Kant、Harpal S. Gill

  DOI：10.1021/ja00238a023

  日期：1987.2
• Soluble-Polymer-Supported Synthesis ofβ-Lactams on a Modified Poly(ethylene glycol)
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi

  DOI：10.1002/(sici)1521-3765(20000103)6:1<133::aid-chem133>3.0.co;2-h

  日期：2000.1.3

  A modified poly(ethylene glycol) (PEG) has been developed for the soluble-polymer-supported synthesis of beta-lactams. The monomethylether of PEG (MeOPEG) with an average M-W of 5000 was used as the support, a 4-(3-propyl)phenyl residue as the spacer, and a 4-oxyphenylamino group as the moiety with the reactive functionality. From this modified PEG representative aromatic, heteroaromatic, unsaturated, and aliphatic imines were obtained in high yields by different procedures. The polymer-supported imines were then employed to prepare several beta-lactams by enolate/imine condensation and ketene/imine cycloaddition. Examples of the control of the absolute stereochemistry during the azetidinone ring formation are also reported. The reactions carried out on the polymer-bound imines showed a remarkable similarity to those performed on nonimmobilized imines, both in terms of yields and stereoselectivities. Removal of the beta-lactams from the polymer has also been accomplished to directly deliver the N-unsubstituted azetidinones.