Janus glycosides of next generation: Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides

Janus glycosides of next generation: Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2019, Volume: 471, Pages: 95-104 Pages count : 10 DOI: 10.1016/j.carres.2018.11.013

Authors

Stepanova Elena V. ^1,2 , Abronina Polina I. ¹ , Zinin Alexander I. ¹ , Chizhov Alexander O. ¹ , Kononov Leonid O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp., 47, 119991, Moscow, Russian Federation
2	Research School of Chemistry & Applied Biomedical Sciences, National Research Tomsk Polytechnic University, Lenin Avenue 30, Tomsk, 634050, Russian Federation

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.

Stepanova E.V. , Abronina P.I. , Zinin A.I. , Chizhov A.O. , Kononov L.O.
Janus glycosides of next generation: Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides
Carbohydrate Research. 2019. V.471. P.95-104. DOI: 10.1016/j.carres.2018.11.013 WOS Scopus OpenAlex

Web of science:	WOS:000453769300012
Scopus:	2-s2.0-85057463841
OpenAlex:	W2903535355

DB	Citing
OpenAlex	19
Scopus	20
Web of science	19