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4-乙酰氧基氮杂环丁酮的合成工艺研究 被引量：4

The synthesis of 4-acetoxyazetidin-2-one
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摘要 以6-氨基青霉烷酸(6-APA)为原料,经溴代、酯化、格氏反应、还原、羟基保护、开环、氧化断裂等步骤得到目标产物,反应总收率达27.9%。 Using 6-aminopenicillanic acid as the starting material,the target molecule 4-acetoxyazetidin-2-one was synthesized through bromination,esterification,the Grignard reaction,reduction,protection,ring-opening and oxidation.The total yield of the product reached 27.9%.
作者 崔振华 郑国钧
机构地区 北京化工大学生命科学与技术学院
出处 《化学试剂》 CAS CSCD 北大核心 2007年第9期569-571,共3页 Chemical Reagents
关键词 6-氨基青霉烷酸 4-乙酰氧基氮杂环丁酮 合成 6-aminopenicillanic acid 4-acetoxyazetidin-2-one synthesis
分类号 TQ463 [化学工程—制药化工]
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参考文献5

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同被引文献37

  • 1杨利敏,王亚明,张松,钟莉,邹文杰.药物中间体7-氨基头孢烷酸的制备[J].天津药学,2005,17(6):1-2. 被引量：8
  • 2Neu H C. Thecrisisinantibiotic-resistance[J].Science, 1992, 257 (5073): 1064-1073.
  • 3Singh G S. Recent progress in the synthesis and chemistry of azetidinones[J], Tetrahedron, 2003, 59:7 631-7 649.
  • 4Bose A K, Banik B K. Stereocontrol of β-lactam formation using microwave irradiation[J]. Tetrahedron Letters, 1995, 36 (22) : 213-216.
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  • 6Banik B K, Becker F F. Unprecedented stereoselectivity in the Staudinger reaction with polyeyclic aromatic imines [ J ]. Tetrahedron Letters, 2000, 41 (34): 6 551-6 554.
  • 7Sasaki A, Goda K. Synthetic studies of carbapenem and penem antibiotics Ⅱ . Synthesis of 3 -acetyl -2 -azetidinone ( 2 +2) cycloaddition of diketene and schiff bases [J]. Chemical Pharmaceutical Bulletin, 1992, 40 (5) : 1 094-1 097.
  • 8Cozzi F, Annunzziata R, Mauro C. A short stereoseleetive synthesis of (3R,4R) -4 -acetoxy -3 -[(R) -1' ((t - butyldirnethylsilyl)oxy)ethyl ]-2-azetidinone, key intermediate for thepreparationofcarbapenemantibiotics[J].Chirality, 1998, 10: 91-94.
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  • 10Nakatsuka T, lwata H, Tanaka R. A facile conversion of the phenylthio group to acetoxy by copperreagents for a practical synthesis of 4-acetoxyazetidin-2-one derivatives from (R) - butane-1,3-diol [J]. Journal of the Chemical Society- Chemical Communnications, 1991, 9: 662-664.

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化学试剂
2007年 第9期

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