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. 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

Jianbin Zheng  1 , Kaveri Balan Urkalan, Seth B Herzon
Affiliations

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

Jianbin Zheng et al. Angew Chem Int Ed Engl. .

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).

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Figures

Scheme 1
Scheme 1
Representative natural products that contain the β-N-glycoside linkage.
Scheme 2
Scheme 2
Synthesis of the N-benzoyl-N-glycoside 5 a. TMS = trimethylsilyl, Bz = benzoyl, THF = tetrahydrofuran, CAN = ceric ammonium nitrate.
See this image and copyright information in PMC

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