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Synthesis of novel di‐ and trisaccharides using enzymatic glycosylation, Dess–Martin oxidation and reductive amination allows rapid access to the target structures. Thus, a novel class of glycomimetics was obtained having nitrogen inserted as bridging atom between two non‐anomeric positions. Novel di‐ and trisaccharide mimetics were designed using N‐acetylglucosamine as a basis structure. A third monosaccharide unit was attached via an unnatural sugar–sugar bond without participation of the anomeric center. Their synthesis, proceeding via oxidation, glycosylation and reductive amination, required only a few steps, thus allowing rapid access to the target structures. Generation of the novel pseudo‐disaccharide was achieved by Dess–Martin oxidation and a subsequent reductive amination. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Synthesis of amino-bridged oligosaccharides using reductive amination opens rapid access to novel glycomimetic target structures as potential ligands for the receptor protein NKR P1 of natural killer cells. Emphasis was laid on fast and facile synthetic routes. The carbonyl building blocks were easily obtained by oxidation with Dess-Martin periodinane or iodoxybenzoic acid (IBX). For the required amino-function-

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