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- W2113419097 abstract "Abstract Two complementary methods for the synthesis of fluorinated exo ‐glycals have been developed, for which previously no general reaction had been available. First, a Selectfluor‐mediated fluorination was optimized after detailed analysis of all the reaction parameters. A dramatic effect of molecular sieves on the course of the reaction was observed. The reaction was generalized with a set of biologically relevant furanosides and pyranosides. A second direct approach involving carbanionic chemistry and the use of N ‐fluorobenzenesulfonimide (NFSI) was performed and this method gave better diastereoselectivities. Assignment of the Z / E configuration of all the fluorinated exo ‐glycals was achieved based on the results of HOESY experiments. Furthermore, fluorinated exo ‐glycal analogues of UDP‐galactofuranose were prepared and assayed against Gl f T2, which is a key enzyme involved in the cell‐wall biosynthesis of major pathogens. The fluorinated exo ‐glycals proved to be potent inhibitors as compared with a series of C ‐glycosidic analogues of UDP‐Gal f , thus demonstrating the double beneficial effect of the exocyclic enol ether functionality and the fluorine atom." @default.
- W2113419097 created "2016-06-24" @default.
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- W2113419097 date "2014-09-24" @default.
- W2113419097 modified "2023-10-18" @default.
- W2113419097 title "Selectfluor and NFSI<i>exo</i>-Glycal Fluorination Strategies Applied to the Enhancement of the Binding Affinity of Galactofuranosyltransferase Gl<i>f</i>T2 Inhibitors" @default.
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- W2113419097 doi "https://doi.org/10.1002/chem.201404180" @default.
- W2113419097 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25251918" @default.
- W2113419097 hasPublicationYear "2014" @default.
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