This contribution explores synthetic routes adopted and optimized for the preparation of three new hexatopic tripodal organic ligands designed for Ln(III) complexation. In these ligands, three strands bearing two pyridyldicarbonyl binding moieties are anchored with a small aliphatic triamine. The described synthesis is not straightforward and depends on the nature of the spacer between coordinating moieties. In addition to the characterisation of targeted ligands, the structure of ditopic intermediates is assessed by X-ray crystallography and discussed with respect to the spacer nature.