Ein neues verfahren zur synthese von desoxyhalogenzuckern

Abstract Addition of carbohydrate derivatives having one free hydroxyl group to aryl cyanates, in the presence of hydrogen chloride, led to the formation of the hydrochlorides of the aryloxycarbonimidoyl derivatives of the starting sugars. These compounds are thermally unstable and decompose to aryl carbamates and the respective chlorodeoxy sugars. From methyl 2,3,4-tri- O -methyl-α- D -glucopyranoside ( 7 ) and 1,2,3,4-tetra- O -acetyl-β- D -glucopyranose ( 9 ) the respective 6-chloro-6-deoxy derivatives 8 and 10 were obtained in high yields. Methyl 3-chloro-3-deoxy-2,4,6-tri- O -methyl-β- D -allopyranoside ( 14 ) was synthesized from methyl 2,4,6-tri- O -methyl-β- D -glucopyranoside ( 13 ) in 17% yield. Compounds 8 and 14 have also been prepared by treatment of 7 and 13 , respectively, with triphenylphosphine in carbon tetrachloride.