Glycosyl azides of sugar 2-sulfonic acids

Ferenc Sajtos, László Lázár, A. Borbás, István Bajza, A. Lipták

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Phenyl and trityl 2-O-sulfonyl-1-thio-α-d-manno- and β-d-glucopyranosides were reacted with sodium azide to yield 2-S-phenyl or 2-S-trityl-d-gluco- and d-mannopyranosyl azides, respectively. Usually, both anomers were formed in approximately equal amounts and formation of glycals was also observed in some cases. The product distribution of these reactions depends on the nature of the aglycone, the applied reagent and also on the solvent. These results can be rationalised by the intermediacy of episulfonium as well as oxocarbenium ions. Oxidation of the 2-S-trityl-α-d-glucopyranosyl or α-d-mannopyranosyl azides by Oxone®, gave sodium 2-sulfonato-α- d-gluco- and α-d-mannopyranosyl azides, respectively.

Original languageEnglish
Pages (from-to)5191-5194
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number31
DOIs
Publication statusPublished - Aug 1 2005

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Sulfonic Acids
Azides
Sugars
Sodium Azide
Sodium
Ions
Oxidation

Keywords

  • Carbohydrate sulfonic acids
  • Glycosyl azides
  • Thiomigration

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Glycosyl azides of sugar 2-sulfonic acids. / Sajtos, Ferenc; Lázár, László; Borbás, A.; Bajza, István; Lipták, A.

In: Tetrahedron Letters, Vol. 46, No. 31, 01.08.2005, p. 5191-5194.

Research output: Contribution to journalArticle

Sajtos, Ferenc ; Lázár, László ; Borbás, A. ; Bajza, István ; Lipták, A. / Glycosyl azides of sugar 2-sulfonic acids. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 31. pp. 5191-5194.
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AU - Lipták, A.

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