New glycosidation reaction 2. preparation of 1-fluoro-d-desosamine derivative and its efficient glycosidation by the use of Cp2HfCl2-AgClO4 as the activator

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Abstract

Preparation of 1-fluoro-D-desosamine derivative 1 and its glycosidation are described. A new activation system for glycosyi fluorides, Cp2 HfCl2-AgCIO4, enables highly efficient glycosidation of 1.

References (15)

  • K. Igarashi

    Adv. Carbohydr. Chem. Biochem.

    (1977)
    A.F. Bochkov et al.
    (1979)
    H. Paulsen

    Angew. Chem. Int. Ed. Engl.

    (1982)
    H. Paulsen

    Chem. Soc. Rev.

    (1984)
  • All new compounds were fully characterized by 1H NMR (400 MHz), IR and high-resolution...
  • S. Masamune et al.
  • See the accompanying communication in this...
  • S. Masamune et al.

    J. Am. Chem. Soc.

    (1975)
    R.B. Woodward

    J. Am. Chem. Soc.

    (1981)
  • K.C. Nicolaou et al.

    J. Am. Chem. Soc.

    (1982)
  • The corresponding bromo sugar is known to be highly unstable even as the HBr salt and also under the glycosidation...
There are more references available in the full text version of this article.

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