The tripodal receptors 1 and 2 based on a triethylbenzene scaffold substituted with trihydroxybenzoyl groups have been synthesised. The conformational preferences and carbohydrate-binding ability of 1 and 2 have been examined by NMR spectroscopy and modelling procedures. The results reveal that the particular structural pre-organisation of 2 facilitates the recognition, in a highly competitive medium (DMSO), of a mannose-based polysaccharide consisting of a linear saccharide chain continuously decorated by α(1 2)-linked branching mannose moieties. By contrast, other α(1 2)-substituted polysaccharides or different monosaccharides are not bound, revealing the selectivity of the interaction. Due to the importance of α(1 2) mannosides, which are abundantly present on the glycan shield of several pathogens, the results reported here open attractive prospects for the potential application of 2 or its derivatives in future antiinfective strategies. ; The Spanish Ministerio de Educación y Ciencia (MEC/MCINN) (project number SAF 2009-13914-C02-01), the Spanish Consejo Superior de Investigaciones Científicas (project number PIF08- 022), the Spanish Comunidad Autónoma de Madrid (CAM) (project number BIPEDD 2-CM-S2010/BMD-2457) and the Spanish Institute of Health Carlos III (ISCIII) (CIBER of Respiratory Diseases, CIBERES) are acknowledged for their financial support.