Solid phase reactions are an alternative to conventional synthesis in solution, especially if these reactions are to be automated. Because of the covalent attachment of the products to the polymer matrix an efficient characterization and purification of intermediates often proves to be challenging. These problems can be overcome by attaching the substrates via hydrophobic interactions. The substrate is bound to an hydrophobic anchor, which binds to reversed-phase silica gel, thus immobilizing the substrate. The strength of the bond to reversed-phase silica gel depends on the surrounding solvent, the size of the anchor and the substrate. Acridone, which has been used as an anchor so far, shows at times insufficient binding to the solid support. Significant amounts of large hydrophilic substrates that are bound to acridone can be found in the liquid phase. To achieve a better immobilization, two new anchor molecules have been synthesized from cholesterol and deoxycholic acid. Different hydrophilic substrates have been bound to these anchors. Methods for binding saccharide structures have been studied in detail. Using these compounds the strength of the bond to reversed phase silica gel of the new anchor molecules has been compared to acridone. Therefor different analysis methods on the basis of HPLC and surface plasmon resonance were developed. The comparism of the interaction with reversed phase silica for the steroid anchors showed a considerable improvement versus acridone.