Interactions between carbohydrate-containing glycoproteins, proteoglycans, and glycolipids on the cell surface are important biological stages for the processes of bacterial or viral infection and tumor metastasis. Moreover, supramolecular interaction by macromolecules with two-fold (C2) or three-fold (C3) geometry is one of the common interactions in many important biological responses. To develop new multivalent symmetrical bioactive compounds or leads, we designed and synthesized several new molecules with these geometries and evaluated their bioactivities in an attempt to find new types of bioactive leads that may interfere with the sugar recognition process. We evaluated bioactivities including antibacterial, antiviral, and anticancer activities of targeted molecules in vitro using biological assay systems. Among the synthesized target derivatives examined, some bivalent symmetrical derivatives showed high levels of bioactivities. In this review, the author describes the results of synthesis of oligovalent symmetrical target compounds and some interesting guiding results of evaluation of their biological activities and structure-activity relationships.