The article examines the challenges and prospects of the legal regulation of the tokenization of real-world assets under the Russian jurisdiction. It analyzes the possibilities of tokenization through digital rights in light of the ongoing digital assets market reform and the Concept for the Tokenization of Real Sector Assets of the Russian Economy. The study concludes that these transformations remove a number of barriers but contain critical contradictions. It identifies challenges including the duplication of the intermediary-based securities market model, the conflict between the reform and the Concept, and the unsuitability of digital rights for tokenizing absolute rights.