C3 Epimerization of Glucose, via Regioselective Oxidation and Reduction

Palladium-catalyzed oxidation can single out the secondary hydroxyl group at C3 in glucose, circumventing the more readily accessible hydroxyl at C6 and the more reactive anomeric hydroxyl. Oxidation followed by reduction results in either allose or allitol, each a rare sugar that is important in bi...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 81; no. 22; pp. 11439 - 11443
Main Authors Jumde, Varsha R, Eisink, Niek N. H. M, Witte, Martin D, Minnaard, Adriaan J
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 18.11.2016
Subjects
Acetylglucosamine - chemistry
Carbon-13 Magnetic Resonance Spectroscopy
Catalysis
Chromatography, Ion Exchange
Glucose - chemistry
Oxidation-Reduction
Proton Magnetic Resonance Spectroscopy
Racemases and Epimerases - chemistry
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Summary:Palladium-catalyzed oxidation can single out the secondary hydroxyl group at C3 in glucose, circumventing the more readily accessible hydroxyl at C6 and the more reactive anomeric hydroxyl. Oxidation followed by reduction results in either allose or allitol, each a rare sugar that is important in biotechnology. Also, N-acetylglucosamine is selectively oxidized at C3. These results demonstrate that glucose and N-acetylglucosamine, the most readily available chiral building blocks, can be versatile substrates in homogeneous catalysis.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b02074