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Volumn , Issue 29, 2007, Pages 4895-4901

Synthesis and glycosidase inhibitory studies of pentahydroxyindolizidines: D-glucose-derived aziridine-2-carboxylate approach

Author keywords

Asymmetric dihydroxylation (AD); Iminosugars; Indolizidine; N methylmorpholine N oxide (NMO)

Indexed keywords


EID: 35349022564     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700461     Document Type: Article
Times cited : (21)

References (61)
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    • For a review on aziridinecarboxylic esters see: D. Tanner, Angew. Chem. Int. Ed. Engl. 1994, 33, 599-619 and references cited therein;
    • a) For a review on aziridinecarboxylic esters see: D. Tanner, Angew. Chem. Int. Ed. Engl. 1994, 33, 599-619 and references cited therein;
  • 2
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    • 2/oxazolines see: J. M. J. Tronchet, M. A. M. Massoud, Heterocycles 1989, 29, 418-426;
    • 2/oxazolines see: J. M. J. Tronchet, M. A. M. Massoud, Heterocycles 1989, 29, 418-426;
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    • J. M. J. Tronchet, E. Winter-Mihaly, M. A. M. Massoud, O. R. Martin, F. Barbalat-Rey, J. Ojha-Poncet, J. Giust, Helv. Chim. Acta 1981, 64, 2350-2354 and references cited therein;
    • c) J. M. J. Tronchet, E. Winter-Mihaly, M. A. M. Massoud, O. R. Martin, F. Barbalat-Rey, J. Ojha-Poncet, J. Giust, Helv. Chim. Acta 1981, 64, 2350-2354 and references cited therein;
  • 4
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    • B. Zwanenburg, Pure Appl. Chem. 1999, 71, 423-430 and references cited therein;
    • d) B. Zwanenburg, Pure Appl. Chem. 1999, 71, 423-430 and references cited therein;
  • 13
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    • For recent accounts on aziridines see
    • m) For recent accounts on aziridines see: I. D. G. Watson, L. Yu, A. K. Yudin, Acc. Chem. Res. 2006, 39, 194-206;
    • (2006) Acc. Chem. Res , vol.39 , pp. 194-206
    • Watson, I.D.G.1    Yu, L.2    Yudin, A.K.3
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    • x) X. E. Hu, Tetrahedron 2004, 60, 2701-2743.
    • (2004) Tetrahedron , vol.60 , pp. 2701-2743
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    • For selected syntheses see: a, Ed, A. Stütz, Wiley-VCH, Weinheim, Germany
    • For selected syntheses see: a) P. C. Tyler, B. G. Winchester, in Iminosugars as Glycosidase Inhibitors (Ed.: A. Stütz), Wiley-VCH, Weinheim, Germany, 1999, p. 125;
    • (1999) Iminosugars as Glycosidase Inhibitors , pp. 125
    • Tyler, P.C.1    Winchester, B.G.2
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    • Ed, A. Brossi, Academic Press, New York
    • A. S. Howard, J. P. Michael, in The Alkaloids (Ed.: A. Brossi), Academic Press, New York, 1986, vol. 28;
    • (1986) The Alkaloids , vol.28
    • Howard, A.S.1    Michael, J.P.2
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    • JP2000072770, CAN 32:203147
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    • The NMR spectra of the dihydroxylated products 9a/9b were very difficult to characterize, due to the doubling of signals as a result of non-homogeneity in the N-CO bond of the urethane functionality.
    • The NMR spectra of the dihydroxylated products 9a/9b were very difficult to characterize, due to the doubling of signals as a result of non-homogeneity in the N-CO bond of the urethane functionality.
  • 52
    • 35349027866 scopus 로고    scopus 로고
    • The mother liquor contained 9a and 9b in a 3:7 ratio.
    • The mother liquor contained 9a and 9b in a 3:7 ratio.
  • 59
    • 35348939675 scopus 로고    scopus 로고
    • As a result of delocalization of the lone pair of electrons on nitrogen bearing the carbonyl group (Cbz) the bulky substituents (CH2Ph and OCH2Ph) at the nitrogen and carbon orient syn to each other. The syn orientation of the substituents is possibly due to the stabilization arising from π-stacking of the phenyl groups. The presence of two distinct isomers of the conjugated ester as a result of delocalization is evident from the 1H NMR spectrum, which showed an isomeric ratio of 58:42
    • 1H NMR spectrum, which showed an isomeric ratio of 58:42.
  • 60
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    • Y.-T. Li, S.-C. Li in Methods in Enzymology (Ed.: V. Ginsberg), Academic Press, 1972, 28, part B, p. 702;
    • Y.-T. Li, S.-C. Li in Methods in Enzymology (Ed.: V. Ginsberg), Academic Press, 1972, vol. 28, part B, p. 702;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.