Abstract
Treatment of 1,2:5,6-di- O-isopropylidene-3- O-toluene- p-sulphonyl-α- d-allofuranose with tetrabutylammonium fluoride in acetonitrile gave 3-deoxy-3-fluoro-1,2:5,6-di- O-isopropylidene-α- d-glucofuranose ( 6) in 74% yield. The structure of 6 was established by a multistage conversion into known 3-deoxy-3-fluoro- d-xylose. Graded hydrolysis of 6 with acid gave 3-deoxy-3-fluoro-1,2- O-isopropylidene-α- d-glucofuranose ( 7), and total hydrolysis gave 3-deoxy-3-fluoro- d-glucose (15–18% overall yield from d-glucose). 3-Deoxy-3-fluoro- d-glucose gave a crystalline β-tetra-acetate and was reconverted into 7 on treatment with acetone in the presence of acid, followed by graded hydrolysis with acid. In a similar manner, 1,2- O-cyclohexylidene-3-deoxy-3-fluoro-α- d-glucofuranose was obtained.
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