N-Glycosyl Amides as Glycosyl Donors in Stereoselective Glycosylation Reactions

Norbert Pleuss; Horst Kunz

doi:10.1055/s-2004-834911

PAPER

N-Glycosyl Amides as Glycosyl Donors in Stereoselective Glycosylation Reactions

Norbert Pleuss, Horst Kunz*
Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
Fax: +49(6131)3924786; e-Mail: hokunz@uni-mainz.de;

Abstract

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Abstract

Due to their high stability, N-glycosyl amides have so far not been considered as glycosyl donors for glycosylation reactions. Two new procedures for the cleavage of the anomeric amide functionality under mild reaction conditions and further stereoselective in situ conversions of the activated glycosyl donors with alcohols and amines to give β-configured O- and N-glycosides are described in this article.

Key words

glycosyl amides - glycosylations - protecting groups - retro Ritter reaction - N-glycosides

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References

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