Abstract
4-Deoxy-4-fluoro- D-glucose ( 5) has been synthesised by two routes. Treatment of 1,6-anhydro-4- O-tosyl-β- D-glucopyranose ( 1) or 1,6:3,4-dianhydro-β- D-galactopyranose ( 2) with potassium hydrogen fluoride in boiling ethane-1,2-diol affords 1,6-anhydro-4-deoxy-4-fluoro-β- D-glucopyranose ( 3). Acid hydrolysis effects the conversion 3 → 5. The dianhydride 2 was readily obtained by photolysis of its 2- O-tosyl derivative. N.m.r. data are given for 5 and the 3-fluoro analogue, and for 2,3,6-tri- O-acetyl-4-deoxy-4-fluoro-α- and -β- D-glucopyranosyl fluoride. Numerous long-range ( 4 J and 5 J) F-H and F-F couplings were observed for these compounds. Treatment of the 2-toluene- p-sulphonate of 3 with base gave 1,6:2,3-dianhydro-4-deoxy-4-fluoro-β- D-mannopyranose ( 10), which was converted into 1,6-anhydro-2,4-dideoxy-2,4-difluoro-β- D-glucopyranose ( 11) by reaction with potassium hydrogen fluoride.
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