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Volumn 64, Issue 1, 1999, Pages 126-132

A stereocontrolled synthesis of monofluoro ketomethylene dipeptide isosteres

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDE; UNCLASSIFIED DRUG;

EID: 0033534729     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981334y     Document Type: Article
Times cited : (18)

References (46)
  • 1
    • 0004060828 scopus 로고
    • ACS Monograph American Chemical Society: Washington, DC
    • Hudlicky, M., Pavlath, A. E., Eds. Chemistry of Organic Fluorine Compounds II; ACS Monograph 187; American Chemical Society: Washington, DC, 1995. See the following chapters: Filler, R.; Kirk, K. Biological Properties of Fluorinated Compounds; Elliott, A. J. Fluorinated Pharmaceuticals; Lang, R. W. Fluorinated Agrochemicals.
    • (1995) Chemistry of Organic Fluorine Compounds II , pp. 187
    • Hudlicky, M.1    Pavlath, A.E.2
  • 2
    • 0010434153 scopus 로고    scopus 로고
    • Hudlicky, M., Pavlath, A. E., Eds. Chemistry of Organic Fluorine Compounds II; ACS Monograph 187; American Chemical Society: Washington, DC, 1995. See the following chapters: Filler, R.; Kirk, K. Biological Properties of Fluorinated Compounds; Elliott, A. J. Fluorinated Pharmaceuticals; Lang, R. W. Fluorinated Agrochemicals.
    • Biological Properties of Fluorinated Compounds
    • Filler, R.K.K.1
  • 3
    • 0004343008 scopus 로고    scopus 로고
    • Hudlicky, M., Pavlath, A. E., Eds. Chemistry of Organic Fluorine Compounds II; ACS Monograph 187; American Chemical Society: Washington, DC, 1995. See the following chapters: Filler, R.; Kirk, K. Biological Properties of Fluorinated Compounds; Elliott, A. J. Fluorinated Pharmaceuticals; Lang, R. W. Fluorinated Agrochemicals.
    • Fluorinated Pharmaceuticals
    • Elliott, A.J.1
  • 4
    • 0003132804 scopus 로고    scopus 로고
    • Hudlicky, M., Pavlath, A. E., Eds. Chemistry of Organic Fluorine Compounds II; ACS Monograph 187; American Chemical Society: Washington, DC, 1995. See the following chapters: Filler, R.; Kirk, K. Biological Properties of Fluorinated Compounds; Elliott, A. J. Fluorinated Pharmaceuticals; Lang, R. W. Fluorinated Agrochemicals.
    • Fluorinated Agrochemicals
    • Lang, R.W.1
  • 6
    • 0000125456 scopus 로고
    • Sammes, P. G., Ed.; Pergamon Press: Oxford, U.K.
    • (b) Rich, D. H. In Comprehensive Medicinal Chemistry; Sammes, P. G., Ed.; Pergamon Press: Oxford, U.K. 1990; pp 391-441.
    • (1990) Comprehensive Medicinal Chemistry , pp. 391-441
    • Rich, D.H.1
  • 7
    • 0003067745 scopus 로고    scopus 로고
    • Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington D.C.
    • (c) Sham, H. L. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington D.C., 1996; pp 184-195.
    • (1996) Biomedical Frontiers of Fluorine Chemistry , pp. 184-195
    • Sham, H.L.1
  • 12
    • 0345442519 scopus 로고    scopus 로고
    • See, for example: (a) Reference 3d.
    • See, for example: (a) Reference 3d.
  • 18
  • 36
    • 0344580420 scopus 로고    scopus 로고
    • note
    • For the combinations used, the reaction of ketoester 8x (derived from amino acid 9x) with triflate 7y gives γ-ketoester 6xy.
  • 37
    • 0345442503 scopus 로고    scopus 로고
    • note
    • For calibrating the LIS method to determine enantioselectivity, racemic 7aa was prepared and subjected to examination by the LIS reagent.
  • 43
    • 0344148910 scopus 로고    scopus 로고
    • note
    • This is based on the very reasonable assumption that epimerization at C-2 or C-5 does not occur during the fluorination.
  • 44
    • 0345011410 scopus 로고    scopus 로고
    • note
    • The semiempirical AM1 calculations were performed on a Silicon Graphics workstation (Indigo 2) using the MOPAC program in Insight II (4.0.0) from MSI. The input geometries for the AM1 calculations were obtained by using the Discover force field (Steepest first 1000 steps and then Newton; Derivative = 0.001) within Insight II (4.0.0).


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