Controlled acid hydrolysis of polymeric chondroitin sulfate of bovine origin afforded in good yield a basic disaccharide fragment that was used for the first time as a starting material for the expeditious preparation of a set of building blocks that in turn act as versatile synthons for the efficient and stereocontrolled construction of a collection of size-defined chondroitin oligomers (from di- to octasaccharides). This step economy process allows their preparation as reducing species, fitted with a fluorophore, or as biotinylated conjugates; all useful tools for the preparation of microarrays, or as probes for the study of the biosynthesis of chondroitin sulfate.