Studies of Aminosugars. XIII. The Synthesis of Paromamine

Paromamine has been synthesized by condensing the N,N′-dinitrophenyl derivative of deoxystreptamine with the N-dinitrophenyl derivative of acetobromoglucosamine in nitromethane in the presence of mercuric salts, and by then removing the protecting groups by treatment with methanolic ammonia and hydrolysis with Dowex 1X2. The synthetic sample was shown to be identical with natural paromamine by a comparison of their infrared spectra and by microbiological assay. The identity was also proved by the determination of the Δ[M]Cu Am values of the tri-N-acetate of the synthetic and natural specimens by the copper-complex methods.