Studies of specifically fluorinated carbohydrates. Part IV. Addition of the elements of "CIF" to D-glucal triacetate

Reaction of chlorine with a suspension of D-glucal triacetate and silver monofluoride in an acetonitrile/benzene solution, affords a mixture of the four possible 2-chloro-2-deoxy-D-glycopyranosyl fluoride triacetates. The structures of these derivatives have been established by nuclear magnetic resonance studies and confirmed by independent syntheses. The major product is 2-chloro-2-deoxy-β-D-glucopyranosyl fluoride triacetate. These results are compared with those from the related "BrF" and "IF" additions.