(R)-3-Chloromethyl-2-[(2R,3R)-2-(4-nitro-benzenesulfonylsulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-3-enoic acid 4-nitro-benzyl ester | 82895-19-0

• 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: (R)-3-Chloromethyl-2-[(2R,3R)-2-(4-nitro-benzenesulfonylsulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-3-enoic acid 4-nitro-benzyl ester
• CAS: 82895-19-0
• 化学式: C₂₉H₂₅ClN₄O₁₀S₂
• 分子量: 689.123
• InChiKey: PFTGQOYBELFASG-STROYTFGSA-N

反应信息

• 作为反应物：
  描述：

  (R)-3-Chloromethyl-2-[(2R,3R)-2-(4-nitro-benzenesulfonylsulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-3-enoic acid 4-nitro-benzyl ester 在 氨 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以52%的产率得到(6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester
  参考文献：
  名称：

  Prominent Aspects of Electroorganic Synthesis in β-Lactam Chemistry

  摘要：

  AbstractThe potentiality of electrolysis procedures in the penicillin‐cephalosporin conversion as well as in the direct transform of penicillins into oxazolineazetidinones as an intermediate for the preparation of the sulfur‐free analogues of cephalosporins are discussed. Especially, a chemoselective electrolytic chlorination of methyl group of 3‐methyl‐3‐butenoate moiety of thiazolineazetidinone derived from penicillins, a direct synthesis of 3′‐thiosubstituted cephalosporins from the thiazoline‐azetidinones, an improved synthesis of exomethylenecephams, an efficient route to 3‐chloromethyl‐Δ3‐cephems, electrochemical S‐S bond fission of 4‐(2‐benzothiazolyldithio) azetidinones, a direct transformation of penicillins into oxazoline‐azetidinones by chloride salt‐promoted electrolysis, and a versatile intermediate for new β‐lactam antibiotics are presented.

  DOI：

  10.1002/bscb.19820911202
• 作为产物：
  描述：

  (R)-3-Methyl-2-[(2R,3R)-2-(4-nitro-benzenesulfonylsulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-3-enoic acid 4-nitro-benzyl ester 以75%的产率得到(R)-3-Chloromethyl-2-[(2R,3R)-2-(4-nitro-benzenesulfonylsulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-3-enoic acid 4-nitro-benzyl ester
  参考文献：
  名称：

  Prominent Aspects of Electroorganic Synthesis in β-Lactam Chemistry

  摘要：

  AbstractThe potentiality of electrolysis procedures in the penicillin‐cephalosporin conversion as well as in the direct transform of penicillins into oxazolineazetidinones as an intermediate for the preparation of the sulfur‐free analogues of cephalosporins are discussed. Especially, a chemoselective electrolytic chlorination of methyl group of 3‐methyl‐3‐butenoate moiety of thiazolineazetidinone derived from penicillins, a direct synthesis of 3′‐thiosubstituted cephalosporins from the thiazoline‐azetidinones, an improved synthesis of exomethylenecephams, an efficient route to 3‐chloromethyl‐Δ3‐cephems, electrochemical S‐S bond fission of 4‐(2‐benzothiazolyldithio) azetidinones, a direct transformation of penicillins into oxazoline‐azetidinones by chloride salt‐promoted electrolysis, and a versatile intermediate for new β‐lactam antibiotics are presented.

  DOI：

  10.1002/bscb.19820911202