Acyloxy tri(isopropoxy)titanium reagents for regioselective cleavage of 2,3-epoxyalcohols. A synthesis of 2-deoxy-d-ribose.

Abstract The cleavage of the oxirane ring of 3,4-anhydro-2-deoxy-D- threo -pentose diethyl acetal by various acetic acid derivatives – titanium(IV) isopropoxide combinations are reported in detail. The high regioselectivity found with tri(isopropoxy)titanium acetate serves as the basis for a synthesis of 2-deoxy-D-ribose and its ethyl furanosides in high yields and optical purity from non-carbohydrate precursors. The synthesis of other acyloxy tri(isopropoxy)titanium reagents is also described.