Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose
| Autor: | Olivier Lessard, Paul A. Johnson, Danny Lainé, Laurie Carrier, Charles-Émile Fecteau, Vincent Denavit, Denis Giguère |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
fluorine effect
Organic Chemistry chemistry.chemical_element Medicinal chemistry Full Research Paper et3n·3hf deoxyfluorination lcsh:QD241-441 Chemistry chemistry Nucleophile lcsh:Organic chemistry Reagent polyfluorinated carbohydrates Nucleophilic substitution Fluorine Reactivity (chemistry) lcsh:Q polyfluoroalditol analogues lcsh:Science |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 16, Iss 1, Pp 2880-2887 (2020) Beilstein Journal of Organic Chemistry |
| ISSN: | 1860-5397 |
| Popis: | In this work, we have developed a simple synthetic approach using Et3N·3HF as an alternative to the DAST reagent. We controlled the stereochemistry of the nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-4-O-triflate-β-ᴅ-talopyranose using Et3N·3HF or in situ generated Et3N·1HF. The influence of the fluorine atom at C2 on reactivity at C4 could contribute to a new fluorine effect in nucleophilic substitution. Finally, with the continuous objective of synthesizing novel multi-vicinal fluorosugars, we prepared one difluorinated and one trifluorinated alditol analogue. |
| Databáze: | OpenAIRE |
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