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Volumn 42, Issue 10, 2003, Pages 1166-1170

Solid-phase-assisted solution-phase synthesis with minimum purification - Preparation of 2-deoxyglycoconjugates from thioglycosides

Author keywords

Functionalized polymers; Glycosidation; Separation techniques; Solid phase synthesis; Thioglycosides

Indexed keywords

FILTRATION; PURIFICATION; SOLUTIONS; SYNTHESIS (CHEMICAL);

EID: 0037429819     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390307     Document Type: Article
Times cited : (33)

References (41)
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    • In analogy to our earlier work we prepared reagent 5 by oxidative ligand transfer of the mobile ligands in [bis(trifluoroacetoxy)iodo]benzene onto polymer-bound iodide. After washing with dry dichloromethane, this new functionalized polymer is obtained, which can be stored at -20°C for weeks: a) G. Sourkouni-Argirusi, A. Kirschning, Org. Lett. 2000, 2, 3781-3784; b) H. Monenschein, G. Sourkouni-Argirusi, K. M. Schubothe, T. O'Hare, A. Kirschning, Org. Lett. 1999, 1, 2101-2104; c) A. Kirschning, H. Monenschein, C. Schmeck, Angew. Chem. 1999, 111, 2720-2722; Angew. Chem. Int. Ed. 1999, 38, 2594-2596.
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    • note
    • Proposed structure is depicted based observations described in ref.[13]
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    • 2-/TMSOTf which all failed to efficiently promote glycosidation.
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    • Pure α-configured thioglycoside 31 was glycosidated with testosterone in the presence of reagent 6. It gave an α/Β mixture of anomers in a 2.3:1 ratio, which was exactly the same ratio found when the Β-configured thioglycoside 31 was employed.
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    • Selectfluor (6) is capable of performing facile nucleophilic addition reactions to glycals: a) M. D. Burkhart, Z. Zhang, S.-C. Hung, C.-H. Wong, J. Am. Chem. Soc. 1997, 119, 11743-11746; b) S. P. Vincent, M.D. Burkart, C.-Y. Tsai, Z. Zhang, C.-H. Wong, J. Org. Chem. 1999, 64, 5264-5279; c) M. Albert, K. Dax, J. Ortner, Tetrahedron 1998, 54, 4839-4848; d) M. Albert, B. J. Paul, K. Dax, Synlett 1999, 1483-1485; e) J. Ortner, M. Albert, H. Weber, K. Dax, J. Carbohydr. Chem. 1999, 18, 297-316.
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    • 0033001712 scopus 로고    scopus 로고
    • Selectfluor (6) is capable of performing facile nucleophilic addition reactions to glycals: a) M. D. Burkhart, Z. Zhang, S.-C. Hung, C.-H. Wong, J. Am. Chem. Soc. 1997, 119, 11743-11746; b) S. P. Vincent, M.D. Burkart, C.-Y. Tsai, Z. Zhang, C.-H. Wong, J. Org. Chem. 1999, 64, 5264-5279; c) M. Albert, K. Dax, J. Ortner, Tetrahedron 1998, 54, 4839-4848; d) M. Albert, B. J. Paul, K. Dax, Synlett 1999, 1483-1485; e) J. Ortner, M. Albert, H. Weber, K. Dax, J. Carbohydr. Chem. 1999, 18, 297-316.
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    • 0032079602 scopus 로고    scopus 로고
    • Selectfluor (6) is capable of performing facile nucleophilic addition reactions to glycals: a) M. D. Burkhart, Z. Zhang, S.-C. Hung, C.-H. Wong, J. Am. Chem. Soc. 1997, 119, 11743-11746; b) S. P. Vincent, M.D. Burkart, C.-Y. Tsai, Z. Zhang, C.-H. Wong, J. Org. Chem. 1999, 64, 5264-5279; c) M. Albert, K. Dax, J. Ortner, Tetrahedron 1998, 54, 4839-4848; d) M. Albert, B. J. Paul, K. Dax, Synlett 1999, 1483-1485; e) J. Ortner, M. Albert, H. Weber, K. Dax, J. Carbohydr. Chem. 1999, 18, 297-316.
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    • 0032860126 scopus 로고    scopus 로고
    • Selectfluor (6) is capable of performing facile nucleophilic addition reactions to glycals: a) M. D. Burkhart, Z. Zhang, S.-C. Hung, C.-H. Wong, J. Am. Chem. Soc. 1997, 119, 11743-11746; b) S. P. Vincent, M.D. Burkart, C.-Y. Tsai, Z. Zhang, C.-H. Wong, J. Org. Chem. 1999, 64, 5264-5279; c) M. Albert, K. Dax, J. Ortner, Tetrahedron 1998, 54, 4839-4848; d) M. Albert, B. J. Paul, K. Dax, Synlett 1999, 1483-1485; e) J. Ortner, M. Albert, H. Weber, K. Dax, J. Carbohydr. Chem. 1999, 18, 297-316.
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    • Albert, M.1    Paul, B.J.2    Dax, K.3
  • 39
    • 0033245426 scopus 로고    scopus 로고
    • Selectfluor (6) is capable of performing facile nucleophilic addition reactions to glycals: a) M. D. Burkhart, Z. Zhang, S.-C. Hung, C.-H. Wong, J. Am. Chem. Soc. 1997, 119, 11743-11746; b) S. P. Vincent, M.D. Burkart, C.-Y. Tsai, Z. Zhang, C.-H. Wong, J. Org. Chem. 1999, 64, 5264-5279; c) M. Albert, K. Dax, J. Ortner, Tetrahedron 1998, 54, 4839-4848; d) M. Albert, B. J. Paul, K. Dax, Synlett 1999, 1483-1485; e) J. Ortner, M. Albert, H. Weber, K. Dax, J. Carbohydr. Chem. 1999, 18, 297-316.
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