Utilizing Staudinger Ligation for the Synthesis of Glycoamino Acid Building Blocks and Other Glycomimetics

Abstract

Abstract The synthesis of amide‐linked glycomimetics is of interest in the glycosciences as they represent a typical linkage in biologically important glycoconjugates. We have addressed the synthesis of three types of N ‐glycosyl amide architectures, which were targeted using Staudinger ligation. This facile method has allowed us to synthesize a collection of N ‐glycosyloctanamides, N ‐glycosyloxyethyl amino acids and multivalent glycoclusters. The last two classes represent molecules that can be used as building blocks in solid‐phase peptide synthesis for the preparation of multivalent glycoconjugates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)