Selective, reductive dechlorination of chlorodeoxy sugars. Structural determination of chlorodeoxy and deoxy sugars by 13C nuclear magnetic resonance spectroscopy

The reductive dechlorination of chlorodeoxy sugars by hydrogenation over Raney nickel in the presence of potassium hydroxide or triethylamine has been investigated; a selective dechlorination was observed in most cases with triethylamine. Several new, chlorodeoxy furanoid derivatives have been synthesized by the use of triphenylphosphine–carbon tetrachloride. 13C magnetic resonance spectroscopy has been employed for the assignment of structure to the chlorodeoxy sugars and the corresponding reduced products.