Novel regioselective, homo-(4–6) and heterogeneous (7–10) dendronized cellulose derivatives have been prepared by the reaction of cellulose in a N,N-dimethylacetamide (DMAc)/LiCl solvent system with diverse dendrons (1–3) possessing an isocyanate focal group. The dendronized cellulose derivatives were characterized using Fourier transform infrared (FTIR), 13 C NMR, thermogravimetric analysis (TGA), and dynamic mechanical thermal analysis (DMTA). These polyfunctionally coated cellulose-based materials showed diverse solubility characteristics in organic solvents ranging from DMAc to methyl alcohol.