Abstract—Benzyl, benzoyl, and acetyl protected 1-OH and 1-SH glycoses in the glucose, glucosamine, galactose, mannose, and lac- tose series react with nitrobenzenes activated by one or two electron withdrawing substituents like nitro and cyano to afford the corresponding aryl glycosides in 50–100% yield. The SNAr displacement of nitrite by 1-OH glycoses is reversible and gives predom- inantly the a-glycosides, whereas 1-SH glycoses do not anomerize and afford the b-glycosides. Thus, the prepared dicyanophenyl gycosides are useful building blocks for the preparation of phthalocyanine-glycoconjugates via template synthesis.
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Keywords: Glycosylation; Aryl glycosides; Nucleophilic