Abstract
3-Amino-polydeoxy disaccharides have been prepared by condensation of a glycal with methyl 2,3,6-trideoxy-α- l- erythro-(or threo-hex-2-enopyranoside in the presence of N-iodosuccinimide. After acid hydrolysis of the glycoside, 1,4-addition of hydrazoic acid to the corresponding hex-2-enopyranose led to 3-azido-disaccharides which were acetylated. Reduction of the azido group gave 2,2′-dideoxy- or 2,2′-dideoxy-2′-iodo compounds. Condensation of O-(3,4-di- O-acetyl-2,6-dideoxy-2-iodo-α- l- manno-hexopyranosyl)-(1 → 4)-1- O-acetyl-2,3,6-trideoxy-3-trifluoroacetamido-α- l- arabino-hexopyranose with daunomycinone, followed by 3′,4′- O-deacetylation produced the new anthracycline, 7- O-[ O-(2,6-dideoxy-2-iodo-α- l- manno-hexopyranosyl)-(1 → 4)-2,3,6-trideoxy-3-trifluoroacetamido-α- l- arabino-dexopyranosyl]-daunomycinone.
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