Synthesis of aminotrideoxybutirosin A, a chemically modified antibiotic active against butirosin-resistant bacteria.

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Abstract
5"-Amino-3'',4'',5"-trideoxybutirosin A (4) was synthesized by 2 routes starting from the known tri-O-acetyl-tetra-N-benzyloxycarbonyl-3",5"-O-cyclohexylidene-3'',4''-di-O-mesylbutirosin A. Introduction of amino function at C-5" was carried out by displacement of 5"-tosyloxy group with sodium azide either before or after 3'',4''-deoxygenation. Compound 4 showed outstanding activities against strains including Pseudomonas aeruginosa and Escherichia coli, which are highly resistant to butirosin and 5"-amino-5"-deoxybutirosin A.

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