O-glycans from the helminth Schistosoma mansoni represent promising leads in the development of immunomodulatory compounds via their interaction with C-type lectin receptors (CLRs), as reported for DC-SIGN, L-SIGN, Langerin and MGL. In this thesis, the chemoenzymatic synthesis of an O-glycan library inspired from structures previously isolated from the helminth will be described. The library will be based on two O-glycan cores, the mucin core 2 and the S.mansoni specific core which will be obtained synthetically. Enzymatic elongations using recombinant glycosyltransferases will enable construction of antigenic epitopes typically observed in the helminth. Synthesized as aminopentyl glycosides, the O-glycans obtained will be printed on-chip for microarray-assisted studies against CLRs.