Oswald Lockhoff, P. Stadler, U. Petersen
May 16, 1983
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Journal
Carbohydrate Research
Abstract
Abstract The aminodisaccharide glycoside methyl 2,4-diamino-2,4-dideoxy-6- O -(2,6-diamino-2,6-dideoxy-α- d -glucopyranosyl)-β- d -glucopyranoside ( 4 ), which exhibits a structural resemblance to neamine, was synthesized via the azido method. Starting from 6- O -acetyl-2-azido-3,4-di- O -benzyl-2-deoxy-α- d -glucopyranosyl bromide, the α- d -glycosylation of O-6 of methyl 2,4-diazido-3- O -benzyl-2,4-dideoxy-β- d -glucopyranoside was accomplished stereoselectively at low temperatures in the presence of mercury bromide. Against some gram-negative test-organisms, the activity of 4 was found to be in the same range as neamine, but directed against different germs.