Abstract
5-Bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-l-talofuranose (7) was obtained by treatment of 3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-d-glucofuranose (3) with N-bromosuccinimide followed by Zemplén O-deacylation and an oxidation-reduction sequence. Nucleophilic displacement of the bromide in 7 with potassium azide readily gave the corresponding 5-azido-5-deoxy-allo derivative 8. Treatment of the 3-trifluoromethanesulphonate of 8 with tris(dimethylamino)sulphonium difluorotrimethylsilicate gave 5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-d-glucofuranose (17. The configuration at C-3 in 17 was confirmed by X-ray crystallography of the 6-benzoate 19.
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