Photochemical Reactions of Carbohydrate Triflates

Abstract

The photochemical reactions of eight carbohydrate trifluoromethanesulfonates (triflates) have been investigated in methanol in the presence of potassium iodide. For those compounds which do not contain an aromatic chromophore, photolysis results in two types of reaction. One type produces deoxy sugars by replacement of the trifluoromethylsulfonyloxy (triflyloxy) group with a hydrogen atom. The second type of reaction generates partially protected sugars by replacement of the trifluoromethylsulfonyl (triflyl) group with a hydrogen atom. When the triflate being irradiated also has a protecting group containing an aromatic ring (i.e., benzyl, benzoyl, or p-tolylsulfonyl group), removal of the protecting group is the exclusive reaction pathway.