The Behavior of Some 2-Acetamido-2-deoxy-furanoses in the Presence of Alkaline Ion-exchange Resin

Abstract

In the presence of an alkaline ion-exchange resin (Amberlite IRA-410), 2-acetamido-2-deoxy-5, 6-O-isopropylidene-3-O-methyl- and -3-O-(tetrahydropyran-2-yl)-D-glucofuranoses, and 2-acetamido-2-deoxy-5, 6-O-isopropylidene-D-allofuranose, as well as 2-acetamido-2-deoxy-5, 6-O-isopropylidene-D-glucofuranose were converted into 2-acetamido-2, 3-dideoxy-5, 6-O-isopropylidene-α-D-erythro-hex-2-enofuranose. The β-elimination was also observed in the case of 2, 5-diacetamido-2, 5-dideoxy-D-xylo- and -D-ribo-furanoses, to give 2, 5-diacetamido-2, 3, 5-trideoxy-D-glycero-pent-2-enofuranose. C-3-Deoxy-furanoses, such as 2-acetamido-2, 3-dideoxy-5, 6-O-isopropylidene-D-arabino- and -D-ribo-hexofuranoses, and 2, 3, 5-triacetamido-2, 3, 5-trideoxy-Dribofuranose, however, did not give β-eliminated compounds under the same condition.