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Volumn 9, Issue 22, 2007, Pages 4455-4458

Synthesis of novel selenapenams, selenacephems, and selenazepines using a 2-(trimethylsilyl)ethyl protection approach

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; AZEPINE DERIVATIVE; BETA LACTAM; ORGANOSELENIUM DERIVATIVE;

EID: 35948989235     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701761t     Document Type: Article
Times cited : (33)

References (48)
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    • For some recent reviews on β-lactam antibiotics, see: a, Morin, R. B, Gorman, M, Eds, Academic Press: New York, Vols
    • For some recent reviews on β-lactam antibiotics, see: (a) Chemical Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.: Academic Press: New York, 1982; Vols. 1-3.
    • (1982) Chemical Biology of β-Lactam Antibiotics , vol.1-3
  • 6
    • 0001729405 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford
    • (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, p 461.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 461
    • Ogawa, A.1    Sonoda, N.2
  • 9
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    • Katritzky, A. R, Meth-Cohn, O, Rees, C. W, Eds, Pergamon: Oxford
    • (d) Dell, C. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 5, p 565.
    • (1995) Comprehensive Organic Functional Group Transformations , vol.5 , pp. 565
    • Dell, C.P.1
  • 10
    • 0000229226 scopus 로고
    • Abel, W. W, Stone, F. G. A, Wilkinson, G, Eds, Pergamon: Oxford
    • (e) Krief, A. In Comprehensive Organometallic Chemistry; Abel, W. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 11, p 515.
    • (1995) Comprehensive Organometallic Chemistry , vol.11 , pp. 515
    • Krief, A.1
  • 12
  • 33
    • 0037140771 scopus 로고    scopus 로고
    • 2-(Trimethylsilyl)ethaneselenol was only once prepared from its diselenide and used for the preparation of ammonium aromatic diselenoates. See: Tani, K.; Murai, T.; Kato, S. J. Am. Chem. Soc. 2002, 124, 5960.
    • 2-(Trimethylsilyl)ethaneselenol was only once prepared from its diselenide and used for the preparation of ammonium aromatic diselenoates. See: Tani, K.; Murai, T.; Kato, S. J. Am. Chem. Soc. 2002, 124, 5960.
  • 37
    • 35948933577 scopus 로고    scopus 로고
    • The use of LHMDS as base was found to be less selective, giving a mixture of two diastereomers in a 1:1.5 ratio.
    • The use of LHMDS as base was found to be less selective, giving a mixture of two diastereomers in a 1:1.5 ratio.
  • 41
  • 45
    • 35948954885 scopus 로고    scopus 로고
    • Chem. Abstr. 1996, 126, 47303.
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  • 46
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    • Recently, Buynak et al. found that the homologue of sulbactam has 10-fold better activity against a class C β-lactamase than does sulbactam itself. See: Buynak, J. D.; Ghadachanda, V. R.; Vogeti, L.; Zhang, H.; Chen, H. J. Org. Chem. 2005, 70, 4510.
    • Recently, Buynak et al. found that the homologue of sulbactam has 10-fold better activity against a class C β-lactamase than does sulbactam itself. See: Buynak, J. D.; Ghadachanda, V. R.; Vogeti, L.; Zhang, H.; Chen, H. J. Org. Chem. 2005, 70, 4510.
  • 47
    • 35948943209 scopus 로고    scopus 로고
    • The reaction time can be shortened by the use of a base such as DIEA, but reaction gave slightly lower yield
    • The reaction time can be shortened by the use of a base such as DIEA, but reaction gave slightly lower yield.
  • 48
    • 35948936474 scopus 로고    scopus 로고
    • Crystallographic data for selenacephem 6, selenapenam 8, and selenacephem 9 have been deposited at the Cambridge Crystallographic Data Centre (deposition no. CCDC-619550 (6), CCDC-619551 (8), and CCDC-619552 (9)). Copies of these data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif.
    • Crystallographic data for selenacephem 6, selenapenam 8, and selenacephem 9 have been deposited at the Cambridge Crystallographic Data Centre (deposition no. CCDC-619550 (6), CCDC-619551 (8), and CCDC-619552 (9)). Copies of these data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.