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Volumn 45, Issue 29, 2004, Pages 5563-5567

From (E)- and (Z)-ketoximes to N-sulfenylimines, ketimines or ketones at will. Application to erythromycin derivatives

Author keywords

Clarithromycin; Erythromycin A; Ketone protecting groups; Macrolide antibiotics; Oximes; Sulfenylimines

Indexed keywords

CLARITHROMYCIN DERIVATIVE; DISULFIDE; ERYTHROMYCIN; IMINE; KETONE DERIVATIVE; OXIME DERIVATIVE; PHOSPHINE DERIVATIVE;

EID: 3042584642     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.002     Document Type: Article
Times cited : (15)

References (38)
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    • For a review, see: Also see Ref. 2 of the preceding paper
    • For a review, see: Corsaro A., Chiacchio U., Pistarà V. Synthesis. 2001;1903. Also see Ref. 2 of the preceding paper
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  • 11
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    • PCT Int. Appl., WO 2002, 050093 A2, 27 June 2002
    • Also see: (b) Lukin, K. A. PCT Int. Appl., WO 2002, 050093 A2, 27 June 2002
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    • note
    • 34NS 332.2412, found 332.2421
  • 14
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    • 2O, in the absence of the phosphine, either in acidic media or in the presence of cyanide ion, required an overnight stirring (Ref. 8). Phenylsulfenylimines are much more resistant to conventional hydrolyses than the corresponding imines. See: Davis F.A., Slegeir W.A.R., Evans S., Schwartz A., Goff D.L., Palmer R. J. Org. Chem. 38:1973;2809
    • (1973) J. Org. Chem. , vol.38 , pp. 2809
    • Davis, F.A.1    Slegeir, W.A.R.2    Evans, S.3    Schwartz, A.4    Goff, D.L.5    Palmer, R.6
  • 15
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    • 3CN. The rapid proton exchange makes both sides of
    • 3CN. The rapid proton exchange makes both sides of 1c magnetically equivalent. For NMR spectra of relevant imines, see: Shoppee C.W., Henderson G.N. J. Chem. Soc., Perkin Trans. 1. 1977;1028
    • (1977) J. Chem. Soc., Perkin Trans. 1 , pp. 1028
    • Shoppee, C.W.1    Henderson, G.N.2
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    • note
    • 13C 2D experiments (HSQC)
  • 19
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    • note
    • 3P under the same conditions
  • 20
    • 0345374756 scopus 로고
    • The E-Z isomerisation energy barriers of N-sulfenyl ketimines are, in general, relatively low (ca. 15-20 kcal/mol, coalescence temperatures around 50-70°C). See:
    • The E-Z isomerisation energy barriers of N-sulfenyl ketimines are, in general, relatively low (ca. 15-20 kcal/mol, coalescence temperatures around 50-70°C). See: Brown C., Grayson B.T., Hudson R.F. Tetrahedron Lett. 1970;4925
    • (1970) Tetrahedron Lett. , pp. 4925
    • Brown, C.1    Grayson, B.T.2    Hudson, R.F.3
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    • For reports from our lab on chemical modifications of erythromycin-like macrolides, see:
    • For reports from our lab on chemical modifications of erythromycin-like macrolides, see: Bartra M., Urpí F., Vilarrasa J. Tetrahedron Lett. 33:1992;3669
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3669
    • Bartra, M.1    Urpí, F.2    Vilarrasa, J.3
  • 34
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    • For a conformational analysis of
    • For a conformational analysis of (E)-6a, see: McGill J.M., Johnson R. Magn. Res. Chem. 31:1993;273
    • (1993) Magn. Res. Chem. , vol.31 , pp. 273
    • McGill, J.M.1    Johnson, R.2
  • 35
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    • note
    • It would be interesting to investigate whether both pathways to (E)-6b from (E)-6a, summarised by means of arrows at the top of Scheme 3, are involved or not. In other words, if (Z)-6b is formed first and it immediately isomerises to (E)-6b, or if (E)-6b comes mainly from the small percentage of (Z)-6a that may be in equilibrium with (E)-6a under the reaction conditions. However, such a study is outside the scope of this communication
  • 37
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    • note
    • +)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.