New syntheses of halogeno- and deoxy-sugars

Abstract

When 3-deoxy-3-hydrazino-1,2:5,6-di-O-isopropylidene-D-allofuranose (III) is oxidised by a solution of iodine in chloroform 3-deoxy-3-iodo-1,2:5,6-di-O-isopropylidene-D-glucofuranose (VI; R = 1) is formed in high yield. N-Iodosuccinimide and iodine–aqueous potassium iodide yield the same product together with the 3-deoxy-3-di-iodo-compound (VII). N-Bromosuccinimide gives the corresponding 3-bromo-derivatives. Periodate or ferricyanide reacts with the hydrazino-compounds (III) to give 3-deoxy-1,2:5,6-di-O-isopropylidene-D-gluco-furanose (IV). In deuterium oxide solution the 3-deoxy-3-deuterioallo-product (VIII) is obtained.