The chemistry of maltose. Part II. Chemical modifications at the reducing unit

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Abstract
Chemical transformations of the reducing unit of maltose have been accomplished by routes starting from the known 1,2,2′,3′,4′,6,6′-hepta-acetate. In particular, the syntheses of 3-chloro-3-deoxy-, 3-azido-3-deoxy-, 2,3-anhydro-, 3,6-anhydro-, and 3-oxo-α-1,4-linked disaccharides are described. The 2,3-anhydride, which has the allo-configuration in the reducing ring, reacted with hydrogen bromide to give the 3-bromo-3-deoxy-maltose derivative by specific diequatorial ring opening. Methyl 4-O-(α-D-glucopyranosyl)-β-D-ribo-hex-3-ulopyranoside hexa-acetate underwent ready epimerisation to give the 2-axial epimer.

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