Two highly hydrophobic Lewis X glycolipids 2 and 3 were prepared. The glycoconjugate 2 was constructed in the following way: pentaerythrytol was used as a distributor on which three racemic phytol hydrophobic chains and a triethyleneglycol spacer β-glycosylated with the pentasaccharide Gal (β 1−4)[Fuc (α 1−3)] GlcNAc (β 1−3) Gal (β 1−4) Glc were anchored. The glycoconjugate 3 was constructed in a similar way, the sugar moiety being the trisaccharide Gal (β 1−4)[Fuc (α 1−3)] GlcNAc, the so-called Lewis X determinant. A triethyleneglycol spacer was used in order to introduce the mobility required for the study of single carbohydrate−carbohydrate interactions. Three phytyl chains increase the hydrophobicity of the lipid moiety compared to the natural ceramide glycolipid 1. These glycolipids display a liquid-expanded behaviour with a high compressibility in monolayer studies. These properties associated with a low solubility in water make them good candidates for the study of the interaction between two Lewis X functionalized vesicles.