Synthesis of the deculopyranosonic acid analog of N-acetylneuraminic acid, its 5-epimer and 6-epimer, and of 5-acetamido-1,3,5-trideoxy-D-glycero-D-galacto-non-2-ulopyranose

Article abstract of DOI:10.1016/0008-6215(92)85008-N

Condensation of 2-acetamido-2-deoxy-5,6-O-isopropylidene-D-mannofuranose with disodium acetonedicarboxylate and subsequent esterification with diphenyldiazomethane yielded diphenylmethyl 6-acetamido-2,4,6-trideoxy-D-glycero-β-D-galacto-dec-3-ulopyranosonat e (3), and its 5- and 6-epimer. Hydrogenation gave the corresponding free acids. Hydrogenation of ester 3 and working-up under alkaline conditions afforded stable ammonium 6-acetamido-2,4,6-trideoxy-D-glycero-β-D-galacto-dec-3-ulopyranosonat e which, on heating, led to an anomeric mixture of 5-acetamido-1,3,5-trideoxy-D-glycero-D-galacto-non-2-ulopyranose. Condensation of 2-acetamido-2-deoxy-5,6-O-isopropylidene-D-mannofuranose with disodium acetonedicarboxylate and subsequent esterification with diphenyldiazomethane yielded diphenylmethyl 6-acetamido-2,4, 6-trideoxy-D-glycero-β-D- galacto-dec-3-ulopyranosonate (3), and its 5- and 6-epimer. Hydrogenation gave the corresponding free acids. Hydrogenation of ester 3 and working-up under alkaline conditions afforded stable ammonium 6-acetamido-2,4,6- trideoxy-D-glycero-β-D-galacto-dec-3- ulopyranosonate which, on heating, led to an anomeric mixture of 5-acetamido-1,3,5-trideoxy-D-glycero-D-galacto-non-2-ulopyranose.