2,5-dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate; CAS No.: 253265-97-3; 2,5-dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate. PROPERTIES: This dioxo-substituted pyrrolidine carbonate features molecular formula C??H??NO? with molecular weight 255.24 g/mol. It typically exists as a white crystalline powder. Soluble in polar aprotic solvents like DMF and DMSO. Melting point approximately 100-105 C. Exhibits IR absorption for carbonate (~1700 cm??) and hydroxyl groups (~3300 cm??). Thermogravimetric analysis indicates decomposition above 180 C under nitrogen. For optimal stability, store at 2-8 C in tightly sealed containers with desiccant, protected from light. The compound may cause mild skin irritation and serious eye damage; therefore, standard laboratory safety precautions including protective clothing and eye protection are recommended during handling. APPLICATIONS: As a dioxo-substituted pyrrolidine carbonate, 2,5-dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate is predominantly utilized in the synthesis of peptide-based therapeutics. It serves as a key building block for constructing bioactive peptides with enhanced conformational stability, particularly in the development of enzyme inhibitors targeting proteases (Journal of Medicinal Chemistry). Additionally, the compound participates in the development of fluorescent probes for bioimaging applications, where its carbonate functionality enables conjugation to biomolecules via esterification reactions (Bioconjugate Chemistry). In materials science, it functions as a monomer for preparing polyurethane foams with enhanced thermal stability, where the pyrrolidine group contributes to improved flame retardancy and mechanical properties (Polymer International).