Synthesis and in vitro antibacterial properties of alkylspectinomycin analogs.

glycosylation of protected actinamine with "fraudulent" sugars followed by C-3' carbonyl generation (by an elimination reaction) and deprotection. We describe here an alternative method of modification at C-6' by elaboration of an activated intermediate 2 which we have prepared2) in three steps from N,N'-dibenzyloxycarbonylactinamine and 3,4,6-tri-Oacetyl 2 deoxy 2 nitroso ƒ¿ L. glucopyranosyl chloride dimer. In vitro antibacterial properties of the 6'-alkylspectinomycins will be compared. The enoneacetate (2)2) reacts cleanly with a mixture of N,N-dimethylformamide and N,Ndimethylformamide dimethylacetal (55°C, 7 hours) to give 94 % yield of enamine (3) after a simple silica gel chromatography. A methanolic solution of enamine (3) is reduced with sodium cyanoborohydride under acidic conditions (methanolic HCI, methyl orange indicator). After extraction from basic solution, the crude amine