Janus glycosides of next generation: Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides. (1st January 2019) - Stepanova, Elena V.
Abstract: Efficient procedures for the preparative synthesis of per- O -acyl derivatives of 4-(3-chloropropoxy)phenyl (CPP) glycosides of a series of common mono- and disaccharides (d -glucose, d -galactose, d -mannose, l -rhamnose, d -arabinofuranose, d -glucosamine, lactose) are described. The CPP glycosides obtained were transformed in almost quantitative yields to the corresponding unprotected 4-(3-azidopropoxy)phenyl (APP) glycosides, which could become next-generation Janus glycosides with cleavable spacer aglycon, ready for conjugation or further transformation. Graphical abstract: Highlights: Protocols for the preparation of Janus glycosides of next generation were developed. Preparative synthesis of 4-(3-chloropropoxy)phenyl (CPP) glycosides is described. Preparative synthesis of 4-(3-azidopropoxy)phenyl (APP) glycosides is described.