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Gold Catalysis in Glycosylation Reactions

Synlett. Bd. 2009. H. 20. Georg Thieme Verlag KG 2009 S. 3346 - 3348

Erscheinungsjahr: 2009

Publikationstyp: Zeitschriftenaufsatz

Sprache: Englisch

Doi/URN: 10.1055/s-0029-1218356

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Inhaltszusammenfassung


Glycosylation of alcohols containing acid-sensitive groups, as for example 1,2-5,6-di-O-isopropylidene-glucofuranose, Fmoc-threonine tert-butyl ester or farnesol, is achieved using glycosyl trichloroacetimidates activated by gold(I) chloride (5-10 mol%). While glycosylation with 2-O-acyl protected glycosyl donors proceeds with 1,2-trans-selectivity, non-neighboring group active glycosyldonors give mixtures of anomeric glycosides or aglycosides depending upon their structure and the reactivity...Glycosylation of alcohols containing acid-sensitive groups, as for example 1,2-5,6-di-O-isopropylidene-glucofuranose, Fmoc-threonine tert-butyl ester or farnesol, is achieved using glycosyl trichloroacetimidates activated by gold(I) chloride (5-10 mol%). While glycosylation with 2-O-acyl protected glycosyl donors proceeds with 1,2-trans-selectivity, non-neighboring group active glycosyldonors give mixtures of anomeric glycosides or aglycosides depending upon their structure and the reactivity of the glycosyl acceptor.» weiterlesen» einklappen

  • gold catalysis
  • glycosylation
  • glycosyl halide

Autoren


Götze, Sebastian (Autor)
Fitzner, Roland (Autor)

Klassifikation


DFG Fachgebiet:

DDC Sachgruppe:
Chemie

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