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Angew Chem Int Ed Engl. 2013 Jun 3;52(23):6068-71. doi: 10.1002/anie.201301264. Epub 2013 Apr 22.

Direct synthesis of β-N-glycosides by the reductive glycosylation of azides with protected and native carbohydrate donors.

Author information

1
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520-8107, USA.

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).

PMID:
23609997
PMCID:
PMC4845733
DOI:
10.1002/anie.201301264
[Indexed for MEDLINE]
Free PMC Article

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