Various Glycosyl Donors with a Ketone or Oxime Function next to the Anomeric Centre: Facile Preparation and Evaluation of their Selectivities in Glycosidations

Frieder W. Lichtenthaler; Ulrich Kläres; Matthias Lergenmüller; Sabine Schwidetzky

doi:10.1055/s-1992-34167

Synthesis 1992; 1992(1/2): 179-184
DOI: 10.1055/s-1992-34167

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Various Glycosyl Donors with a Ketone or Oxime Function next to the Anomeric Centre: Facile Preparation and Evaluation of their Selectivities in Glycosidations

Frieder W. Lichtenthaler^* , Ulrich Kläres, Matthias Lergenmüller, Sabine Schwidetzky

^*Institut für Organische Chemie, Technische Hochschule Darmstadt, Petersenstraße 22, D-6100 Darmstadt, Germany

Abstract

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An efficient one-pot procedure is described for the conversion of a variety of hydroxyglycal esters to their 2-oxoglycosyl bromides which simply comprises of brief treatment with N-bromosuccinimide/methanol at ambient temperature. Exhibiting comparably low anomeric reactivity in glycosidation reactions, these ulosyl bromides, as well as their 2-benzoyloxyimino analogs, can readily be transformed into a range of more reactive glycosyl donors with iodine, pentenyloxy, ethylthio and dithiocarbamoyl residues at the anomeric centre, such that any ß-selective glycosidation may be successfullv achieved.

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