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Transformation of Sugars into Chiral Polyols over a Heterogeneous Catalyst
Author(s) -
Tamura Masazumi,
Yuasa Naoto,
Cao Ji,
Nakagawa Yoshinao,
Tomishige Keiichi
Publication year - 2018
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.201803043
Subject(s) - synthon , vicinal , chemistry , hemiacetal , catalysis , diol , transformation (genetics) , stereochemistry , combinatorial chemistry , polyol , organic chemistry , biochemistry , polyurethane , gene
Transformation of sugars, while maintaining the intrinsic stereochemical structure, is desirable. However, such a transformation requires multistep synthesis with protection and deprotection of the OH groups. Herein, a new method for selective transformation of sugar derivatives into chiral building blocks and a diol synthon, with retention of the intrinsic configuration (stereo‐ and regioselectively), is demonstrated. The method is based on the selective recognition of cis ‐vicinal OH groups in sugars and leads to the one‐pot removal of the cis ‐vicinal OH groups, without protection of OH groups (except the OH group of the hemiacetal group), over a heterogeneous CeO 2 ‐supported ReO x and Pd (ReO x ‐Pd/CeO 2 ) catalyst by using H 2 as a reducing agent.