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

• Published in: Angewandte Chemie International Edition Vol. 59; no. 7; pp. 2755 - 2759
• Main Authors: Masuda, Yusuke, Tsuda, Hiromu, Murakami, Masahiro
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 10-02-2020
• Edition: International ed. in English
• Subjects: aldose; Benzophenone; Bioactive compounds; Carbon; deoxy sugar; Isomerization; Lactones; Oxidation; photoreaction; water; benzophenone; deoxy sugar; water; photoreaction; aldose
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201914242

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.
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.