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Synthesis of a terminal A-B-C disaccharide fragment of flambamycin, curamycin, and avilamycin.

Carbohydr Res

October 1993

Institut für Organische Chemie, Rheinisch-Westfälischen Technischen Hochschule Aachen, Germany.

Methyl 2,6-dideoxy-4-O-[2,6-dideoxy-4-O-(3,5-dichloro-4-hydroxy-2-methoxy-6- methylbenzoyl)-beta-D-arabino-hexopyranosyl]-alpha-D-arabino-he xopyranoside (25) corresponds to an A-B-C disaccharide subunit of the title antibiotics. It was synthesized from suitably protected monosaccharide and aromatic precursors. The readily available 4,6-O-benzylidene-1,2-O-(R)-propylidene-alpha-D-glucopyranose was converted in six steps into 2-O-acetyl-4-O-benzoyl-3-O-benzyl-6-deoxy-alpha-D-glucopyranosyl bromide, which was condensed with methyl 3-O-benzyl-2,6-dideoxy-alpha-D-arabino-hexopyranoside in the presence of mercury(II) cyanide.

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