Abstract A potential monosaccharidic mimetic of the sialyl Lewis X tetrasaccharide (sLe X) was identified based on an in silico docking study using the crystal structure of an E-selectin- sLe X complex. The chemical synthesis of the mimetic in an ortho-selective C-glycosylation is described. This compound and two close analogues were evaluated in a cell-based selectin binding assay where none of the tested mimetics showed an IC50 below 1mM. ...