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Keywords:

  • Glycosylation;
  • Stereoselec­tivity;
  • Sialic acids;
  • Hydrogen bonds;
  • ­Amides

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)