AbstractStepwise solution syntheses are described of the homo‐oligomers Z‐(Thr)n‐NHCH3(n=1–4,I1–4), Z‐{[Gal(Ac)4β]Thr}n‐NHCH3(n=1–5,II1–5) and Z‐[(Galβ)Thr]n‐NHCH3(n=1−5,III1–5). Members of theIII1–5series were obtained by de‐acetylation of the corresponding oligomers of theII1–5series. The conformational preferences of the terminally protected homo‐peptides of the three series were investigated by FT‐IR absorption spectroscopy both in the solid state and in CDCl3solution, at various concentrations. Proton NMR measurements in CDCl3and in DMSO‐d6were also carried out and the effect of temperature variation on the chemical shifts of amide protons was determined in DMSO‐d6(range 298–335 K) and in CDCl3(range 298–320 K). CD spectra were recorded in water and in TFE. Solubility problems prevented measurements in CDCl3solution for Z‐(Thr)4‐NHCH3and for the entireIII1–5series. The existence of unordered structures in the carbohydrate‐free oligomers and of more or less extended, organized structures in the glycosylated derivatives is indicated by the NMR and IR measurements. The sugar moieties apparently show a structure‐inducing effect on the peptide chain