New approach to aminoglycoside antibiotics

Abstract
Photobromination of peracylated hexopyranoses and treatment of the resultant 5-bromo-derivatives with zinc and acetic acid afforded 6-deoxy-5-enose esters which, with mercury(II) salts in aqueous media, gave 2-deoxyinosose triesters; applied to β-D-maltose octa-acetate, these procedures afforded an α-glucosylated inosose derivative which on further α-glycosylation gave a ‘pseudotrisac-charide’ related to those upon which aminoglycoside antibiotics are based.

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