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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Published in | Journal of organic chemistry Vol. 81; no. 22; pp. 11439 - 11443 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
United States
American Chemical Society
18.11.2016
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Subjects | |
Online Access | Get full text |
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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. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.6b02074 |