ChemInform Abstract: SYNTHESIS OF A MASKED DERIVATIVE OF 3′-DEOXYDIHYDROSTREPTOBIOSAMINE, A PRECURSOR FOR THE SYNTHESIS OF 3′-DEOXYDIHYDROSTREPTOMYCIN

2′-N-Acetyl-4′,6′-di-O-acetyl-3,3a-O-carbonyl-3′-deoxydihydrostreptobiosamine (15), a precursor in the synthesis of 3″-deoxydihydrostreptomycin, was prepared from benzyl α-dihydrostreptobiosaminide. The synthesis involves formation of L-allo compound (5) with inversion of the 3′-hydroxyl group of L-gluco derivative (2) in order to facilitate 3′-chlorination, dechlorination, of the 3′-chloro-L-gluco derivative (7 or 11) with tributyltin hydride, and utilization of cyclic 3,3a-O-carbonyl group instead of 3,3a-O-isopropylidene group which was unstable in the later reactions.