<p>This work presents the synthesis of hyperbranched oligohydroxyethylaminourea(methyl)urethanes of the second, third and fourth generations by a two-step divergent scheme using triethanolamine, dimethyl carbonate and monoethanolamine. The proposed method provides high yields of the target products (95.56–97.74%). The structure of the synthesized compounds was confirmed by a comprehensive analysis using IR spectroscopy, NMR (¹H, ¹³C), titrimetry and elemental analysis, which made it possible to reliably determine the composition of functional groups (OH – 5, 9, 17; NH – 4, 8, 16), molecular weight (697, 1318, 2459 g/mol) and the degree of branching of molecules (0.875, 0.88, 0.91) for the 2nd, 3rd and 4th generations. Thermogravimetric analysis revealed high thermal stability of the oligomers up to 135–137°C, while X-ray diffraction analysis revealed an amorphous phase state with partial crystallinity in the fourth-generation macromolecules. Molecular modeling using the PM3 method demonstrated an increase in macromolecular size with increasing generation, while DLS and SEM methods revealed a spherical particle morphology exceeding the size of single molecules due to intermolecular bonding. The obtained results open up prospects for the application of the synthesized hyperbranched oligomers in catalysis, active substance carriers, and other areas of materials science requiring structurally controlled polymer systems with controlled properties.</p>