A novel reagent for regioselective cleavage of 2,3-epoxyalcohols by fluoride - a synthesis of 3-fluoro-293-dideoxy-d-erythro-pentose.

Abstract The cleavage of the oxirane ring of 3,4-anhydro-2deoxy-D- threo -pentose diethyl acetal by (isopropoxy)-titanium fluorides is discussed. The high regioselectivity found with bis(isopropoxy)titanium difluoride is the basis for an enantioselective synthesis of 3-fluoro-2,3-deoxy-D- erythreo -pentose from a non-carbohydrate precursor.