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Schalli, M; Thonhofer, M; Wolfsgruber, A; Weber, H; Fischer, R; Saf, R; Stütz, AE.
From secondary alcohols to tertiary fluoro substituents: A simple route to hydroxymethyl branched sugars with a fluorine substituent at the branching point.
Carbohydr Res. 2016; 436(15): 11-19.
Doi: 10.1016/j.carres.2016.10.013
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- Leading authors Med Uni Graz
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Schalli Michael
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From a secondary hydroxyl group, by the simple sequence of oxidation, Wittig reaction of the obtained ulose with methoxymethylene triphenyl phosphorane, exposure of the resulting exocyclic enol ether to Selectfluor and subsequent reduction of the α-fluoro aldehyde thus obtained, tertiary fluoro substituents can be introduced into carbohydrate and carbohydrate-related scaffolds at a branching point now bearing a new hydroxymethyl group.
Copyright © 2016 Elsevier Ltd. All rights reserved.
- Find related publications in this database (using NLM MeSH Indexing)
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Alcohols - chemistry
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Carbohydrates - chemistry
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Fluorides - chemistry
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Fluorine - chemistry
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Molecular Structure -
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Oxidation-Reduction -
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Stereoisomerism -
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Branched-chain fluorosugar
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Selectfluor
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Electrophilic fluorination
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Synthesis