Direct Synthesis of [beta]-N-Glycosides by the Reductive Glycosylation of Azides with Protected and Native Carbohydrate Donors

A simple and straightforward method for the stereocontrolled synthesis of [beta]-linked N-glycosides uses alkyl and aryl azides as the nitrogen source. The N-glycosides are formed in high yields and with high [beta] selectivities (typically >70% yield, >15:1 [beta]:α selectivity). This approac...

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Veröffentlicht in:	Angewandte Chemie International Edition 2013-06, Vol.52 (23), p.6068-6071
Hauptverfasser:	Zheng, Jianbin, Urkalan, Kaveri Balan, Herzon, Seth B
Format:	Artikel
Sprache:	eng
Schlagworte:	Amino acids Aromatic compounds Carbohydrates Peptides Selectivity Synthesis
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description	A simple and straightforward method for the stereocontrolled synthesis of [beta]-linked N-glycosides uses alkyl and aryl azides as the nitrogen source. The N-glycosides are formed in high yields and with high [beta] selectivities (typically >70% yield, >15:1 [beta]:α selectivity). This approach is also amenable to the synthesis of N-glycosylated amino acids and peptides (see example, Fmoc=9-fluorenylmethoxycarbonyl).
doi_str_mv	10.1002/anie.201301264
format	Article
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subjects	Amino acids Aromatic compounds Carbohydrates Peptides Selectivity Synthesis
title	Direct Synthesis of [beta]-N-Glycosides by the Reductive Glycosylation of Azides with Protected and Native Carbohydrate Donors
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