Carbohydrate Research p. 249 - 264 (1988)
Update date:2022-07-31
Topics:
Kuszmann, Jaanos
Maatron-Mereesz, Magdolna
Jerkovich, Gyula
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.
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