Synthesis of 3,5-O-Benzylidene-2-deoxy-L-riboaldose from 5,5-Dihydroxy-2-phenyl-1,3-dioxane

Abstract

The asymmetric alkylation of 2-phenyl-1,3-dioxan-5-one was achieved via the RAMP-hydrazone. Regeneration of the ketone followed by setreoselective reduction and ozonolysis, gave the protected 2-deoxy-L-ribose, 3,5-O-benzyldiene-2-deoxy-L-erythro-pentoaldose with 98% e.e. Removal of the benzylidene yielded the unnatural 2-deoxy-L-ribose.