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

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 oxazoline protected sugar derivatives. The structural diversity at the anomeric carbon was explored by stereoselective chemical glycosidation. The oxazoline 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 the synthesis of multifunctionalized complex glycocon­jugates via click reactions.