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C1 Oxidation/C2 Reduction Isomerization of Unprotected Aldoses Induced by Light/Ketone
Author(s) -
Masuda Yusuke,
Tsuda Hiromu,
Murakami Masahiro
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201914242
Subject(s) - isomerization , anomer , benzophenone , chemistry , ketone , photochemistry , carbon fibers , irradiation , hydrogen , organic chemistry , medicinal chemistry , catalysis , materials science , nuclear physics , composite material , physics , composite number
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.