APPLICATION OF THE BUCHERER REACTION TO CARBOHYDRATE DERIVATIVES

Article abstract of DOI:10.1016/0008-6215(88)84147-8

The Bucerer reaction of carbohydrate derivatives having a free carbonyl group proceeds normally, giving mainly the expected spiro-hydantoin derivatives.With derivatives having a free aldehydo group attached to an acetal ring in an α-position, the acetal ring is opened via an elimination reaction yielding unsaturated hydantoin derivatives.These reactions were studied using 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose, 2,3:4,5-di-O-isopropylidene-D-arabinose, -D-ribose, and -D-xylose, 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose, 1,2-O-isopropylidene-3-O-methyl-α-D-xylo-pentodialdo-1,4-mannofuranose, 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose, and 2,3:4,5-di-O-isopropylidene-β-D-arabino-hexosulo-2,6-pyranose.