Abstract
4-Acetamido-4,5-dideoxy- l-xylofuranose (IV), a sugar having a ring nitrogen in the five-membered (pyrrolidine type) ring structure, was synthesized. Desulfurization of 2-acetamido-2-deoxy-3,4- O-isopropylidene- d-glucose diethyl dithioacetal (I) gave 2-acetamido-1,2-dideoxy-3,4- O-isopropylidene- d-glucitol (II). Periodic acid oxidation of II gave 4-acetamido-4,5-dideoxy-2,3- O-isopropylidene- l-xylose (III), shown to have the aldehydo structure and characterized as the benzylphenylhydrazone. Hydrolysis of III with aqueous acetic acid removed the O-isopropylidene group, and the product was shown by n.m.r. and infrared spectral data to exist principally in the cyclic furanoid form.
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