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Volumn 44, Issue 19, 2003, Pages 3775-3779

Synthesis of α- and β-C-glycosides of N-acetylglucosamine

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINOSUGAR; GLYCOSIDE; METAL; N ACETYLGLUCOSAMINE;

EID: 0037420740     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00818-9     Document Type: Article
Times cited : (23)

References (40)
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    • Postema, M.H.D.1
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    • For reviews see: (a) Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, 1995; (b) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Elsevier Science: Oxford, 1995; (c) Du, Y.; Linhardt, R. J. Tetrahedron 1998, 54, 9913-9959.
    • (1995) The Chemistry of C-Glycosides
    • Levy, D.E.1    Tang, C.2
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    • For reviews see: (a) Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, 1995; (b) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Elsevier Science: Oxford, 1995; (c) Du, Y.; Linhardt, R. J. Tetrahedron 1998, 54, 9913-9959.
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    • For a recent review
    • For a recent review: Dondoni A., Marra A. Chem. Rev. 100:2000;4395-4421.
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    • For some additional recent examples, see: (a) Lohof, E.; Planker, E.; Mang, C.; Burkhart, F.; Dechantsreiter, M. A.; Haubner, R.; Wester, H.-J.; Schwaiger, M.; Holzemann, G.; Goodman, S. L.; Kessler, H. Angew. Chem., Int. Ed. 2000, 39, 2761-2764; (b) SanMartin, R.; Tavassoli, B.; Walsh, K. E.; Walter, D. S.; Gallagher, T. Org. Lett. 2000, 2, 4051-4054; (c) Cipolla, L.; La Ferla, B.; Lay, L.; Peri, F.; Nicotra, F. Tetrahedron: Asymmetry 2000, 11, 295-303; (d) Schafer, A.; Thiem, J. J. Org. Chem. 2000, 65, 24-29; (e) Pachamuthu, K.; Gupta, A.; Das, J.; Schmidt, R. R.; Vankar, Y. D. Eur. J. Org. Chem. 2002, 1479-1483.
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    • Lohof, E.1    Planker, E.2    Mang, C.3    Burkhart, F.4    Dechantsreiter, M.A.5    Haubner, R.6    Wester, H.-J.7    Schwaiger, M.8    Holzemann, G.9    Goodman, S.L.10    Kessler, H.11
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    • For some additional recent examples, see: (a) Lohof, E.; Planker, E.; Mang, C.; Burkhart, F.; Dechantsreiter, M. A.; Haubner, R.; Wester, H.-J.; Schwaiger, M.; Holzemann, G.; Goodman, S. L.; Kessler, H. Angew. Chem., Int. Ed. 2000, 39, 2761-2764; (b) SanMartin, R.; Tavassoli, B.; Walsh, K. E.; Walter, D. S.; Gallagher, T. Org. Lett. 2000, 2, 4051-4054; (c) Cipolla, L.; La Ferla, B.; Lay, L.; Peri, F.; Nicotra, F. Tetrahedron: Asymmetry 2000, 11, 295-303; (d) Schafer, A.; Thiem, J. J. Org. Chem. 2000, 65, 24-29; (e) Pachamuthu, K.; Gupta, A.; Das, J.; Schmidt, R. R.; Vankar, Y. D. Eur. J. Org. Chem. 2002, 1479-1483.
    • (2000) Org. Lett. , vol.2 , pp. 4051-4054
    • SanMartin, R.1    Tavassoli, B.2    Walsh, K.E.3    Walter, D.S.4    Gallagher, T.5
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    • 0034002291 scopus 로고    scopus 로고
    • For some additional recent examples, see: (a) Lohof, E.; Planker, E.; Mang, C.; Burkhart, F.; Dechantsreiter, M. A.; Haubner, R.; Wester, H.-J.; Schwaiger, M.; Holzemann, G.; Goodman, S. L.; Kessler, H. Angew. Chem., Int. Ed. 2000, 39, 2761-2764; (b) SanMartin, R.; Tavassoli, B.; Walsh, K. E.; Walter, D. S.; Gallagher, T. Org. Lett. 2000, 2, 4051-4054; (c) Cipolla, L.; La Ferla, B.; Lay, L.; Peri, F.; Nicotra, F. Tetrahedron: Asymmetry 2000, 11, 295-303; (d) Schafer, A.; Thiem, J. J. Org. Chem. 2000, 65, 24-29; (e) Pachamuthu, K.; Gupta, A.; Das, J.; Schmidt, R. R.; Vankar, Y. D. Eur. J. Org. Chem. 2002, 1479-1483.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 295-303
    • Cipolla, L.1    La Ferla, B.2    Lay, L.3    Peri, F.4    Nicotra, F.5
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    • 0033984349 scopus 로고    scopus 로고
    • For some additional recent examples, see: (a) Lohof, E.; Planker, E.; Mang, C.; Burkhart, F.; Dechantsreiter, M. A.; Haubner, R.; Wester, H.-J.; Schwaiger, M.; Holzemann, G.; Goodman, S. L.; Kessler, H. Angew. Chem., Int. Ed. 2000, 39, 2761-2764; (b) SanMartin, R.; Tavassoli, B.; Walsh, K. E.; Walter, D. S.; Gallagher, T. Org. Lett. 2000, 2, 4051-4054; (c) Cipolla, L.; La Ferla, B.; Lay, L.; Peri, F.; Nicotra, F. Tetrahedron: Asymmetry 2000, 11, 295-303; (d) Schafer, A.; Thiem, J. J. Org. Chem. 2000, 65, 24-29; (e) Pachamuthu, K.; Gupta, A.; Das, J.; Schmidt, R. R.; Vankar, Y. D. Eur. J. Org. Chem. 2002, 1479-1483.
    • (2000) J. Org. Chem. , vol.65 , pp. 24-29
    • Schafer, A.1    Thiem, J.2
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    • For some additional recent examples, see: (a) Lohof, E.; Planker, E.; Mang, C.; Burkhart, F.; Dechantsreiter, M. A.; Haubner, R.; Wester, H.-J.; Schwaiger, M.; Holzemann, G.; Goodman, S. L.; Kessler, H. Angew. Chem., Int. Ed. 2000, 39, 2761-2764; (b) SanMartin, R.; Tavassoli, B.; Walsh, K. E.; Walter, D. S.; Gallagher, T. Org. Lett. 2000, 2, 4051-4054; (c) Cipolla, L.; La Ferla, B.; Lay, L.; Peri, F.; Nicotra, F. Tetrahedron: Asymmetry 2000, 11, 295-303; (d) Schafer, A.; Thiem, J. J. Org. Chem. 2000, 65, 24-29; (e) Pachamuthu, K.; Gupta, A.; Das, J.; Schmidt, R. R.; Vankar, Y. D. Eur. J. Org. Chem. 2002, 1479-1483.
    • (2002) Eur. J. Org. Chem. , pp. 1479-1483
    • Pachamuthu, K.1    Gupta, A.2    Das, J.3    Schmidt, R.R.4    Vankar, Y.D.5
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    • 1H NMR
    • 1H NMR.
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    • To our knowledge, this represents the first such epimerization of a 2-deoxy-2-amino sugar. See
    • To our knowledge, this represents the first such epimerization of a 2-deoxy-2-amino sugar. See: Kobertz W.R., Bertozzi C.R., Bednarski M.D. Tetrahedron Lett. 33:1992;737-740.
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    • Kobertz, W.R.1    Bertozzi, C.R.2    Bednarski, M.D.3
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    • Even the typically reliable Nozaki reagent led to poor yields and isomerization
    • Even the typically reliable Nozaki reagent led to poor yields and isomerization: Hibino J.I., Okazoe T., Kazuhiko T., Nozaki H. Tetrahedron Lett. 26:1985;5579-5580.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5579-5580
    • Hibino, J.I.1    Okazoe, T.2    Kazuhiko, T.3    Nozaki, H.4
  • 40
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    • note
    • abstract


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.