Synthesis of Functionalized Amphiphilic Glycoconjugates and Glycoclusters

Glycolipids are involved in many cellular recognition processes, so there is a need for their synthesis as well as for the design and preparation of glycolipid mimetics. In addition to the application of glycolipid mimetics in a glycobiological context, they are also of interest in many other fields of research, due to their amphiphilic characters. Our goal was to elaborate a series of known orthogonally functionalized glycomimetics and cluster glycosides into glycomimetics of a glycolipid type, so monosaccharide building blocks such as 3 , glycodendrons such as 19 , and branched cluster glycosides of the type 24 were ligated with lipophilic molecules by peptide coupling, this conjugation providing a new class of complex amphiphilic glycoconjugates with high molecular diversity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)