期刊文献+

(5S,6R)-2-(4-甲基)苯基-6-[(1R)-叔丁基二甲基硅氧乙基]-青霉烯-3-羧酸乙酯的合成研究

Synthesis of ethyl(5S,6R)-2-(4-methylphenyl)-6-[(1R)-tert-butyldimethylsilyloxyethyl]-penem-3-carboxylate
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摘要 A compound ethyl(5S,6R)-2-(4-methylphenyl)-6-[(1R)-tert-butyldimethylsilyloxyethy]-penem-3-carboxylate was synthesized through displacement,acylation and Wittig cyclization reaction of optically active material(3R,4R)-3-[(1R)-tert-butyldimethylsilyloxyethyl]-4-acetoxy-2-azetidi-none(4AA)upon thionocarboxlic acid.The intermediates and the target product were characterized by 1HNMR,IR,elementary analysis and MS. A compound ethyl(5S,6R)-2-(4-methylphenyl)-6-[(1R)-tert-butyldimethylsilyloxyethy]-penem-3-carboxylate was synthesized through displacement,acylation and Wittig cyclization reaction of optically active material(3R,4R)-3-[(1R)-tert-butyldimethylsilyloxyethyl]-4-acetoxy-2-azetidi-none(4AA)upon thionocarboxlic acid.The intermediates and the target product were characterized by 1HNMR,IR,elementary analysis and MS.
出处 《化学研究与应用》 CAS CSCD 北大核心 2010年第8期1054-1057,共4页 Chemical Research and Application
基金 河北省自然科学基金资助项目(B2005000007)
关键词 青霉烯 4AA (5S 6R)-2-(4-甲基)苯基-6-[(1R)-叔丁基二甲基硅氧乙基]-青霉烯-3-羧酸乙酯 合成 penem 4AA ethyl(5S 6R)-2-(4-methylphenyl)-6-[(1R)-tert-butyldimethylsilyloxyethyl]-pene-m-3-carboxylate synthesis
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参考文献10

  • 1Perboni B,Rossi T,Donati D,et al.Tribactama:a novel class of β-lactam antibiotics.bently pH,ponsford red.recent advances in the chemistry of antiinfective agents[M].Cambridge:The Royal Society of Chemisty,1993:21-66.
  • 2韩红娜,刘浚.青霉烯类抗生素的研究进展[J].中国新药杂志,2001,10(5):331-334. 被引量:8
  • 3MARTEL A,DEXTRAZE P,DARIS J P,et al.Nuclear analogs of β-lactam antibiotics.XIV.Synthesis of pen-ems via(4-tritylthio-2-azetidinon-1-yl)triphenylpho-s-phoranylidene acetates[J].Can.J.Chem.,1982,60(7):942-944.
  • 4GIRIJAVALLABHAN V M,GANGULY A,Liu Y,et al.A new class of penems-2-N-substituted compounds synthesis and antibacterial activity[J].J.Antibiot,1986,39(8):1187-1190.
  • 5PERRONE E,ALPEGIANI M,BEDESCHI A,et al.The carbonyl-carbonyl coupling route to penems:a stepwise analysis[J].Tetrahedron Lett.,1984,25(22):2399-2402.
  • 6Alfred J C,Scott L D,Norma K D et al.Dual-action penems and carbapenems[J].J.Med.Chem.,1992,35(3),1828-1839.
  • 7Lang M,Prasad D K,Holick W,et al.The penems,a new class of β-lactam antibiotics.2.total synthesis of racemic 6-unsubstituted representatives[J].J.Am.Chem.Soc.,1979,101(21):6296-6301.
  • 8Connolly S,Moore K W,Cooke M D,et al.The synthesis and biological activity of a novel series of 2-aryl penems[J].J.Antibiot.,1991,44(10):1169-1171.
  • 9Cabri W,Candiani H,Zarini F,et al.Zinc halides-mediated nucleophilic attack of thioacid salts in non protic media.A key step in the total synthesis of penems[J].Tetrahedron Lett.,1994,35(20):3379.
  • 10Rie T,Yoshiaki O,Seiichi I,et al.Structure-activity relationships of penem antibiotics:crys-tallographic structures and implications for their antimicrobial activities[J].Bioorg.Med.Chem.,1997,5(7):1389-1399.

二级参考文献22

  • 1[12]Mealy N,Castaner J.Solupenem[J].Drugs Future,1996,21(7)∶706-710.
  • 2[13]Watan K,Kato N,Tanaka-bandoh K,et al.In vitro activities of sulopenem,a new parenteral penem[J].Jpn J Antibiot,1996,49(4)∶367-376.
  • 3国井乙彦,齐藤厚,熊泽净一,他.TMA-230の前期临床第I相实验成绩[J].日本化学疗法学会杂志,1995,43(6):655.
  • 4[15]Corraz AJ, Dax SL,Dunlap NK,et al.Dual-action penems and carbapenems[J].J Med Chem,1992,35(10)∶1828-1839.
  • 5[16]Anton FE,Christine CS.Structure-activity studies of quinolone-penems in genetically defined strains of Escherichia coli[J].Antimicrob Agents Chemother,1997,41(11)∶2570-2572.
  • 6[17]Fabio V,Elena P,Massimo DL,et al.In vitro antibacterial activity of men 10700,a new penem antibiotic[J].Chemotherapy,1999,45(6)∶405-410.
  • 7[18]Hamilton-Miller JMT,Shah S.Comparative anti-anaerobic activity of men-10700,a penem antibiotic[J].Int J Antimicrob Agents,1998,10(4)∶321-324.
  • 8[19]Hamilton-Miller JMT,Shah S.In vitro microbiological assessment of a new penem, men 10700[J].J Antimicrob Chemother,1997,39(5)∶575-584.
  • 9[20]Andre M,Philippe L,Didier M.Kinetic study of interaction between BRL 42715, β-lactamase,and D-alanyl-D-alanine peptidases[J].Antimicrob Agents Chemother,1995,39(1)∶227-231.
  • 10[21]Bubulychev IM,Stephen AL.Penem BRL-42715:an effective inactivator for β-Lactamase[J].J Am Chm Soc,1995,117(1)∶479.

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