DPPS

CAS 170278-50-9, Cat. No EN300-255940
Reagent for the conversion of azides into the diazo compounds

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1-[3-(Diphenylphosphino)-propanoyl]-2,5-pyrrolidindione (DPPS) is a phosphine-based reagent primarily used for the conversion of azides into diazo compounds under mild conditions. This transformation proceeds via the formation of an acyl triazene intermediate, which undergoes fragmentation in the presence of mild bases such as aqueous sodium bicarbonate, producing diazo compounds with excellent yields and functional group tolerance¹. It has been successfully applied in the synthesis of key intermediates, such as diazoamide derivatives in total syntheses like aperidine². Phosphine-functionalized gramicidin S derivatives created using DPPS have been explored as ligands in asymmetric catalysis, demonstrating its versatility in expanding catalytic methodologies³. DPPS is a white solid with a melting point of 104–108°C, soluble in most organic solvents, and stable under standard storage conditions⁴.

Synonyms: N-succinimidyl 3-(diphenylphosphino)propionate; 2,5-dioxopyrrolidin-1-yl 3-(diphenylphosphanyl)propanoate; DPPS; (2,5-dioxopyrrolidin-1-yl) 3-diphenylphosphanylpropanoate; 3-(diphenylphosphino)propionic acid N-succinimidyl ester; 1-{[3-(diphenylphosphanyl)propanoyl]oxy}pyrrolidine-2,5-dione; 1-[3-(diphenylphosphino)-1-oxopropoxy]-2,5-pyrrolidinedione; 2,5-dioxo-1-pyrrolidinyl 3-(diphenylphosphino)propanoate; 3-(diphenylphosphino)propanoic acid N-succinimidyl ester; N-succinimidyl 3-(diphenylphosphino)propanoate