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Synthesis 1997; 1997(2): 159-161
DOI: 10.1055/s-1997-3181
short paper
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Organofluorine Compounds and Fluorinating Agents; 18:1 Trifluoromethylzinc Bromide as a Reagent for the Preparation of Glycosyl Fluorides

Ralf Miethchen* , Christian Hager, Martin Hein
  • *Department of Organic Chemistry, University of Rostock, Buchbinderstraße 9, D-18051 Rostock, Germany, Fax: +49(381)4981763; E-mail: ralf.miethchen@chemie.uni-rostock.de
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Publication Date:
31 December 2000 (online)

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Trifluoromethylzinc bromide was used to prepare the corresponding glycosyl fluorides from the peracetylated α-pyranosyl bromides of D-glucose 1, D-galactose 3, D-mannose 5, D-lyxose 7, and L-rhamnose 9, respectively, in good yields. D-Glucopyranosyl bromide 1 and the D-galactopyranosyl bromide 3, exclusively delivered the corresponding β-D-glycosyl fluorides 2 β and 4 β. The other bromides 5, 7 and 9 formed mixtures of anomeric fluorides (6 α/6 β, 8 α/8 β, 10 α/10 β). Similarly, the anomeric OH-groups of the D-glycopyranoses 11, 12, 13, 15, 17 could be substituted by fluoride using trifluoromethylzinc bromide/titanium tetrafluoride. In all cases mixtures of anomeric fluorides 2 α/2 β, 6 α/6 β, 14 α/14 β, 16 α/16 β, and 18 α/18 β were obtained.

pyranoses - glycosyl bromides - substitution - glycosyl fluorides