Abstract
The aminocyclitol antibiotic neamine has been chemically modified at the hydroxyl group on C-6 of the 2-deoxystreptamine moiety. The partially acetylated neamine derivatives, 6,3′,4′-tri- O-acetyl- ( 3) and 5,3′,4′-tri- O-acetyl-1,3,2′,6′-tetra- N-(ethoxycarbonyl)neamine ( 4), were prepared by random hydrolysis of the 5,6- O-ethoxyethylidene derivative ( 2), followed by chromatographic purification. Condensation of 4 and 2,3,5-tri- O-benzoyl- d-ribofuranosyl chloride led to 6- O-(β- d-ribofuranosyl)neamine ( 7). Analogous condensation of 4 with 2,3,4,6-tetra- O-acetyl-α- d-glucopyranosyl bromide or 2,3,4,6-tetra- O-acetyl-α- d-galactopyranosyl bromide afforded the corresponding 6- O-( d-hexopyranosyl)neamines.
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