Synthesis of Methyl Aprabiosaminide and 2-Hydroxyapramycin from Apramycin

We describe a protocol for the selective cleavage of the 2-deoxystreptamine ring from the structurally unusual aminoglycoside antibiotic apramycin, enabling for the first time the preparation of aprabiosamine derivatives. We further describe reglycosylation of the aprabiosamine core with a selectively protected optically pure streptamine derivative, giving, after deprotection, 2-hydroxyapramycin, the first apramycin derivative functionalized at the 2 position.