C1 Oxidation/C2 Reduction Isomerization of Unprotected Aldoses Induced by Light/Ketone.

ABSTRACT

Unprotected aldoses in water undergo an isomerization reaction via a radical pathway when irradiated with light in the presence of water-soluble benzophenone. Whereas its anomeric carbon (C1) is oxidized to a carboxy group, the hydroxy group on the C2 carbon is replaced by hydrogen. The generated 2-deoxy lactones are readily reduced to the corresponding 2-deoxy aldoses, which are often contained in bioactive compounds.