Janus glycosides of next generation: Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides. (1st January 2019)

• Record Type: Journal Article
• Authors: Stepanova, Elena V.; Abronina, Polina I.; Zinin, Alexander I.; Chizhov, Alexander O.; Kononov, Leonid O.
• Is Part Of: Carbohydrate research. Volume 471(2019)
• Page Start: 95
• Page End: 104
• Publication Date: 2019-01-01
• Subjects: Glycosylation -- Spacer aglycon -- Janus aglycon -- Cleavable aglycon; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2018.11.013
• Languages: English
• ISSNs: 0008-6215

Abstract

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.