Get access

Stereoselectivity of Glycosylation May Change During the Reaction Course: Highly α-Stereoselective Sialylation Achieved by Supramer Approach

Authors

  • Leonid O. Kononov,

    1. N. K. Kochetkov Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russian Federation, Fax: +7-499-137-6148
    Search for more papers by this author
  • Nelly N. Malysheva,

    1. N. K. Kochetkov Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russian Federation, Fax: +7-499-137-6148
    Search for more papers by this author
  • Anna V. Orlova

    1. N. K. Kochetkov Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russian Federation, Fax: +7-499-137-6148
    Search for more papers by this author

Abstract

The stereoselectivity of NIS/TfOH-promoted glycosylation with O-acetylated N-acetylneuraminic acid phenyl thioglycoside was found to be dependent on the reaction time. Highly α-stereoselective sialylation (27:1 anomer ratio) was achieved by decreasing the reaction time (from 3 h to 15 min) and by adding a non-reacting compound (1 equiv.) capable of modifying the structure of hydrogen-bonded supramolecular aggregates (supramers) of the glycosyl donor. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Ancillary