Organofluorine Compounds and Fluorinating Agents; 18:1 Trifluoromethylzinc Bromide as a Reagent for the Preparation of Glycosyl Fluorides

Ralf Miethchen; Christian Hager; Martin Hein

doi:10.1055/s-1997-3181

Synthesis 1997; 1997(2): 159-161
DOI: 10.1055/s-1997-3181

short paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

PDF Download All articles of this category

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

PDF (291 kb)