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

Jianbin Zheng, Kaveri Balan Urkalan, Seth B. Herzon*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

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 βselectivities (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).

Original languageEnglish (US)
Pages (from-to)6068-6071
Number of pages4
JournalAngewandte Chemie - International Edition
Volume52
Issue number23
DOIs
StatePublished - Jun 3 2013

Keywords

  • Wittig reactions
  • aspartylation
  • glycosides
  • glycosylation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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