A general and efficient route to 3′-deoxy-3′-N-, S-, and C-substituted altropyranosyl thymines from 2′,3′-O-anhydro-mannopyranosylthymine

Abstract An efficient route to 1-(2,3- O -anhydro-4,6- O -phenylmethylene-β- d -mannopyranosyl) thymine from 1,2,4,6-tetra- O -acetyl-3- O -tosyl-β- d -glucopyranose has been devised. This newly synthesized epoxide is opened up regioselectively at the C-3′-position by N -, S -, and C -nucleophiles to afford a wide range of new 3′-deoxy-3′-substituted altropyranosyl thymines.