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Volumn 3, Issue 21, 2001, Pages 3393-3396

β-Selective glycosylations with masked D-mycosamine precursors

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; CHOLESTEROL; HEXOSAMINE; MACROLIDE; MYCOSAMINE;

EID: 0035909642     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016617i     Document Type: Article
Times cited : (35)

References (28)
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    • The first step proceeded in 40% yield on the basis of 50% recovered aglycon
    • The first step proceeded in 40% yield on the basis of 50% recovered aglycon.
  • 8
    • 0000503477 scopus 로고
    • Cavender, C. J.; Shiner, V. J. J. Org. Chem. 1972, 37, 3567-3569. Vasella, A.; Witzig, C.; Chiara, J.-L.; Martin-Lomas, M. Helv. Chem. Acta 1991, 74, 2073-2076. Alper, P. B.; Hung, S.-C.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029-6032.
    • (1972) J. Org. Chem. , vol.37 , pp. 3567-3569
    • Cavender, C.J.1    Shiner, V.J.2
  • 9
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    • Cavender, C. J.; Shiner, V. J. J. Org. Chem. 1972, 37, 3567-3569. Vasella, A.; Witzig, C.; Chiara, J.-L.; Martin-Lomas, M. Helv. Chem. Acta 1991, 74, 2073-2076. Alper, P. B.; Hung, S.-C.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029-6032.
    • (1991) Helv. Chem. Acta , vol.74 , pp. 2073-2076
    • Vasella, A.1    Witzig, C.2    Chiara, J.-L.3    Martin-Lomas, M.4
  • 10
    • 0030593609 scopus 로고    scopus 로고
    • Cavender, C. J.; Shiner, V. J. J. Org. Chem. 1972, 37, 3567-3569. Vasella, A.; Witzig, C.; Chiara, J.-L.; Martin-Lomas, M. Helv. Chem. Acta 1991, 74, 2073-2076. Alper, P. B.; Hung, S.-C.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029-6032.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6029-6032
    • Alper, P.B.1    Hung, S.-C.2    Wong, C.-H.3
  • 11
    • 0043232723 scopus 로고    scopus 로고
    • A TBS protecting group was not robust enough for the chemistry to follow
    • A TBS protecting group was not robust enough for the chemistry to follow.
  • 12
    • 0001359363 scopus 로고
    • Blomberg, L.; Norberg, T. J. Carbohydr. Chem. 1992, 11, 751-760. Meerwein, H.; Zenner, K.-F.; Gipp, R. Liebigs Ann. Chem. 1965, 688, 67-77.
    • (1992) J. Carbohydr. Chem. , vol.11 , pp. 751-760
    • Blomberg, L.1    Norberg, T.2
  • 14
    • 0043232722 scopus 로고    scopus 로고
    • The axial isomer could not be separated from impurities
    • The axial isomer could not be separated from impurities.
  • 24
    • 0031462601 scopus 로고    scopus 로고
    • Lichtenthaler, F. W.; Klares, U.; Szurmai, Z.; Werner, B. Carbohydr. Res. 1998, 305, 293-303. Lichtenthaler, F. W.; Metz, T. W. Tetrahedron Lett. 1997, 38, 5477-5480. Lichtenthaler, F. W.; Jarglis, P.; Hempe, W. Liebigs Ann. Chem. 1983, 1959-1972.
    • (1998) Carbohydr. Res. , vol.305 , pp. 293-303
    • Lichtenthaler, F.W.1    Klares, U.2    Szurmai, Z.3    Werner, B.4
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    • Lichtenthaler, F. W.; Klares, U.; Szurmai, Z.; Werner, B. Carbohydr. Res. 1998, 305, 293-303. Lichtenthaler, F. W.; Metz, T. W. Tetrahedron Lett. 1997, 38, 5477-5480. Lichtenthaler, F. W.; Jarglis, P.; Hempe, W. Liebigs Ann. Chem. 1983, 1959-1972.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5477-5480
    • Lichtenthaler, F.W.1    Metz, T.W.2
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    • Lichtenthaler, F. W.; Klares, U.; Szurmai, Z.; Werner, B. Carbohydr. Res. 1998, 305, 293-303. Lichtenthaler, F. W.; Metz, T. W. Tetrahedron Lett. 1997, 38, 5477-5480. Lichtenthaler, F. W.; Jarglis, P.; Hempe, W. Liebigs Ann. Chem. 1983, 1959-1972.
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  • 27
    • 0042230430 scopus 로고    scopus 로고
    • The TBS protecting group is necessary since both C4 acetates and benzoates are eliminated upon oxidation of the C2 alcohol
    • The TBS protecting group is necessary since both C4 acetates and benzoates are eliminated upon oxidation of the C2 alcohol.
  • 28
    • 0043232721 scopus 로고    scopus 로고
    • 2; therefore, following an aqueous workup, it is used directly in the next step
    • 2; therefore, following an aqueous workup, it is used directly in the next step.


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