Synthesis of 1,3-divalent glycoconjugates with diverse structure and functionalization

Laxminarayan Sahoo, Anadi Singhamahapatra, Satyanarayan Sahoo

Abstract


A series of novel 1,3-difunctionalized glycoconjugates were synthesized using a sequence of regioselective functionalization and stereoselective glycosidation of D-glucose and D-GlcNAc. Regioselective C-3 functionalization of sugar molecules was achieved by chemical functionalization of isopropylidene or oxazolidene protected sugar derivatives. Structural diversity at the anomeric carbon was explored by stereoselective chemical glycosidation. Oxazolidene protected D-GlcNAc derivative gave either pyranose or furanose derivatives on glycosidation depending on the amount of Lewis acid used. The diversely functionalized glycoconjugates with azide or alkyne groups are potentially useful for synthesis of multifunctionalized complex glycoconjugates by click reaction.

Keywords


glycoconjugate; regioselective; stereoselective; chemical synthesis; click reaction, glycolipids

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DOI: https://doi.org/10.2298/JSC170905030S

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