Studies on the Glycosylation of N-Acetylneuraminic Acid

Abstract

Glycal derivatives of N-acetylneuraminic acid were prepared and their N-iodosuccinimide-mediated glycosylation shown to proceed only with most reactive alcohols, Their reduced enol ether reactivity is attributed to the α unsaturated ester reature. Thus several reduced glycal derivatives were synthesized. These couid be glycosyiatec with simple alcohols as well as otner saccnarides as aglycones in averaae to modest yields with the trans-diaxiai additions compounas prevailing. A number or selective and specific prepparation led to both the anomeric phenylthioglycosides or N dcety Ineuraminic acid. These could be used in phenylmercurl triflate-promoted glycosylations to afford several derivatives.