278 research outputs found
Data for 19F MAS-NMR Membrane Partition Experiments
No full textSupporting information for 2023 Angewandte Chimie paper:
Wang, Z., Felstead, H. R., Troup, R. I., Linclau, B., & Williamson, P. (2023). Lipophilicity modulations by fluorination correlate with membrane partitioning. Angewandte Chemie International Edition, [e202301077]. https://doi.org/10.1002/anie.202301077</span
Data for the paper 'Minimising conformational bias in fluoroprolines through vicinal difluorination'
No full textRaw data for the paper “Minimising conformational bias in fluoroprolines through vicinal difluorination”, authored by Gert-Jan Hofman, Emile Ottoy, Mark E. Light, Bruno Kieffer, Ilya Kuprov, José C. Martins, Davy Sinnaeve and Bruno Linclau.</span
Dataset for Synthesis of vicinal dideoxy-difluorinated galactoses
No full textDataset supports the paper:
Julien Malassis, Jean-Baptiste Vendeville, Qui-Hien Nguyen, Marie Boujon, Quentin Gaignard-Gaillard, Mark Light, Bruno Linclau
(Accepted/In press). Synthesis of vicinal dideoxy-difluorinated galactoses. Organic & Biomolecular Chemistry. DOI: 10.1039/c9ob00707e</span
Data for 'Synthesis and conformational properties of 3,4-difluoro-L-prolines'
No full textData supporting the paper:
Hofman, G-J., Ottoy, E., Light, M., Kieffer, B., Martins, J. C., Kuprov, I., ... Linclau, B. (2019). Synthesis and conformational properties of 3,4-difluoro-L-prolines. Journal of Organic Chemistry. DOI: 10.1021/acs.joc.8b02920
</span
Enantioselective dihydroxylation of perfluoroalkyl-substituted alkenes
No full textThis contribution gives an overview of the literature regarding the Sharpless Asymmetric Dihydroxylation of alkenes which contain a perfluoroalkyl (RF = CnF2n+1) or a perfluoroalkylidene (R(CF2)n) substituent (hereafter termed “fluorinated alkenes”). Modifications required for these unreactive substrates towards OsO4-mediated dihydroxylation are highlighted, as well as a comparison of enantioselectivities with the corresponding nonfluorinated alkenes
The synthesis and glycoside formation of polyfluorinated carbohydrates
No full textFluorinated carbohydrates have found many applications in the glycosciences. Typically, these contain fluorination at a single position. There are not many applications involving polyfluorinated carbohydrates, here defined as monosaccharides in which more than one carbon has at least one fluorine substituent directly attached to it, with the notable exception of their use as mechanism-based inhibitors. The increasing attention to carbohydrate physical properties, especially around lipophilicity, has resulted in a surge of interest for this class of compounds. This review covers the considerable body of work toward the synthesis of polyfluorinated hexoses, pentoses, ketosugars, and aminosugars including sialic acids and nucleosides. An overview of the current state of the art of their glycosidation is also provided.</p
A convenient AIBN-initiated radical addition of ethyl iododifluoroacetate to alkenes
No full textThe AIBN-initiated addition of ethyl 4-iodo-2,2-difluoroacetate to a variety of alkene substrates is described. The addition generally led to the corresponding addition products in good to excellent yields and various functional groups could be tolerated under the reaction conditions
Glycosylation of vicinal di- and trifluorinated glucose and galactose donors
No full textThe acid-catalysed formation of glycosidic bonds is more difficult when glycosyl donors are fluorinated, especially at the 2-position. Here we report high-yielding glycosidation and glycosylation reactions of 2,3-difluorinated- and 2,3,4-trifluorinated gluco- and galactopyranoside donors with a variety of acceptors under conventional trichloroacetimidate/TMSOTf activation in moderate to high anomeric selectivities. This methodology allows access to highly fluorinated glycans, illustrated with the synthesis of a pentafluorinated disaccharide
Data for 'A synthesis of 2,3,4-trideoxy-2,3,4-trifluoroglucose'
No full textData supports the publication:
Quiquempoix, L. G., Wang, Z., Graton, J., Latchem, P. G., Light, M., Le Questel, J-Y., & Linclau, B. (2019). A synthesis of 2,3,4-trideoxy-2,3,4-trifluoroglucose. Journal of Organic Chemistry. DOI: 10.1021/acs.joc.9b00310</span
A mild, phosphine-free method for the conversion of alcohols into halides (Cl, Br, I) via the corresponding O-alkyl isoureas
No full textA novel procedure for the conversion of primary and secondary alcohols into the corresponding alkyl chlorides, bromides and iodides is described. The transformation is high-yielding in the case of chlorides and bromides, tolerates a range of functional groups, and does not rely on the use of phosphines
- …
