Synthesis of fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides

János Kerékgyártó, Károly Ágoston, G. Batta, Johannis P. Kamerling, Johannes F G Vliegenthart

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Fully O-benzylated mono-, di- and trisaccharide glycosyl azides representing the reducing terminal of the core structure of N-glycans were synthesized. Totally and partially benzylated thioalkyl glucosamine glycosides were converted into the corresponding glycosyl azides with trimethylsilyl azide in the presence of methyl triflate. The β-mannosidic linkage was created by C-2 epimerization of the initially introduced β-D- gluco-unit via oxidation followed by stereoselective reduction with tetrabutylammonium borohydride.

Original languageEnglish
Pages (from-to)7189-7192
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number39
DOIs
Publication statusPublished - Sep 24 1998

Fingerprint

Azides
Glycopeptides
Glycosides
Trisaccharides
Disaccharides
Glucosamine
Polysaccharides
Oxidation
methyl triflate
tetrabutylammonium borohydride
azidotrimethylsilane

Keywords

  • Azides
  • Carbohydrates
  • Glycosidation
  • Thioglycosides

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides. / Kerékgyártó, János; Ágoston, Károly; Batta, G.; Kamerling, Johannis P.; Vliegenthart, Johannes F G.

In: Tetrahedron Letters, Vol. 39, No. 39, 24.09.1998, p. 7189-7192.

Research output: Contribution to journalArticle

Kerékgyártó, János ; Ágoston, Károly ; Batta, G. ; Kamerling, Johannis P. ; Vliegenthart, Johannes F G. / Synthesis of fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides. In: Tetrahedron Letters. 1998 ; Vol. 39, No. 39. pp. 7189-7192.
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