Aminocyclitols. XVII. A Facile Synthesis of 2-Deoxystreptamine

Bromination of myo-inosadiamine-l,3 dihydrochloride or its di-N-acetyl derivative with acetyl bromide and acetic anhydride yielded pentaacetyl-2-bromo-2-deoxy-scyllo-inosadiamine-1,3 (III), which upon reductive debromination afforded pentaacetyl-2-deoxystreptamine (IV). The configurations of the new compounds obtained were established by nuclear magnetic resonance and chemical evidences. A mechanism of the bromination reaction is presented, based on the configuration of the bromo-compound.