A peracetylated β-D-N-acetyllactosamine (LacNAc; Galβ1-4GlcNAc) ligand equipped with an azide handle through a hydrophilic, discrete triethylene glycol (PEG3) spacer, with the sugar hydroxyl groups protected as acetate esters. The peracetate groups increase lipophilicity to facilitate cell membrane permeability. The azide can be covalently coupled to alkynes via copper-catalyzed azide-alkyne cycloaddition (CuAAC) or to dibenzocyclooctyne (DBCO) and related strained alkynes via copper-free click chemistry, forming stable 1,2,3-triazole linkages. LacNAc is a core disaccharide of N- and O-glycans and a ligand for galectins; it is also a substrate for sialyltransferases and fucosyltransferases, enabling extension to sialylated and fucosylated structures. In its peracetylated form, the probe is also suited to metabolic glycoengineering and cell-based studies where membrane permeability is required.