The synthesis of the lipophilic docosyltri(hex-1-ynyl)tin was achieved in three steps according to twodifferent synthetic pathways. This compound reacted with nonporous silica to yield surface-modifiedsilica via the loss of the three alkynyl functionalities and the formation of Sibulk-O-Sn-C bonds. Thereactivity and the maximum chain loading reached were compared to those obtained with theheptadecafluorodecyltin analogue. The differences observed were rationalized in terms of electronic demandand cross-sectional area of the grafted chain, as evidenced by FTIR spectroscopy and X-ray crystalstructures of the precursors.