Integrated route to the L-aldohexoses using a common man-made chiral building block.

Abstract

Starting from a common man-made chiral sugar building block, five out of eight L-aldohexoses have been synthesized in a diastereocontrolled manner to complete an integrated synthesis of the eight possible aldohexoses; the remaining three L-hexoses were synthesized from the same building block. Thus, L-altrose, L-mannose, L-allose, L-talose, and L-glucose were obtained in the present investigation on the basis of the inherent convex-face selectivity exerted by the chiral building block.