Alkyl 1-Thio-α-D-glucofuranosiduronamideの合成

抄録

Application of alkanethiol to methyl β-D-glucofuranosiduronolactone (I) and acetylation of the resulting D-glucuronolactone dialkyl dithioacetal (II) afforded 2, 4, 5-tri-O-acetyl-D-glucuronolactone dialkyl dithioacetal (III). Treatment of (II) and (III) with ammonia and acetylation of its product, D-glucuronamide dialkyl dithioacetal (IV) gave 2, 3, 4, 5-tetra-O-acetyl-D-glucuronamide dialkyl dithioacetal (V). (IV) and (V) were also obtained directly from D-glucuronamide.
Partial dethiolation of (IV) afforded alkyl 1-thio-α-D-glucofuranosiduronamide (VII) whose acylation gave alkyl thic-2, 3, 5-tri-O-acetyl-α-D-glucofuranosiduronamide (VIII). This cyclized structure was confirmed by periodate oxidation, Weerman test, and from infrared spectrum.
By the reaction of methyl 1-bromo-1-deoxy-2, 3, 4-tri-O-acetyl-α-D-glucopyranuronate (XII) and 1-bromo-1-deoxy-2, 3, 4-tri-O-acetyl-α-D-glucopyranuronamide (IX) with sodium ethylmercaptide, ethyl 1-thio-β-D-glucopyranosiduronamide (XI) was prepared.