title: Direct synthesis of β-N-glycosides by the reductive glycosylation of azides with protected and native carbohydrate donors.
abstract: A simple and straightforward method for the stereocontrolled synthesis of β-linked N-glycosides uses alkyl and aryl azides as the nitrogen source. The N-glycosides are formed in high yields and with high β selectivities (typically >70% yield, >15:1 β:α selectivity). This approach is also amenable to the synthesis of N-glycosylated amino acids and peptides (see example, Fmoc=9-fluorenylmethoxycarbonyl).
authors.affiliation: Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520-8107, USA.
authors.forename: Jianbin
authors.initials: J
authors.lastname: Zheng
authors.forename: Kaveri Balan
authors.initials: KB
authors.lastname: Urkalan
authors.forename: Seth B
authors.initials: SB
authors.lastname: Herzon
mesh_terms: D001386:Azides / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation
chemical_list: D001386:Azides; D002241:Carbohydrates; D006027:Glycosides