We present the synthesis of so called amphiphilic glycomacromolecules (APGs) by using solid-phase polymer synthesis. Based on tailor made building blocks, monodisperse APGs with varying compositions are synthesized, introducing carbohydrate side chains and crosslinkable units at defined positions within the macromolecule. Self-assembly of the APGs is characterized via spectroscopic as well as scattering techniques and reveals structural dependencies between APG composition and self-assembly behavior such as the formation of spherical vs. worm-like micelles. Furthermore, polymerizable units within the APGs allow for fixation of the self-assembled structures. Carbohydrate presenting micelles are then evaluated as inhibitors of bacterial adhesion demonstrating their potential for biomedical applications.