C1 Oxidation/C2 Reduction Isomerization of Unprotected Aldoses Induced by Light/Ketone
Dr. Yusuke Masuda
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorHiromu Tsuda
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Masahiro Murakami
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorDr. Yusuke Masuda
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorHiromu Tsuda
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Masahiro Murakami
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510 Japan
Search for more papers by this authorAbstract
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.
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