Synthesis of fluorinated thiodigalactoside analogues
| Autor: | Denis Giguère, Christina Leclerc, Jacob St-Gelais |
|---|---|
| Rok vydání: | 2022 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Organic Chemistry Galactose General Medicine 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Thiogalactosides 0104 chemical sciences 3. Good health Analytical Chemistry chemistry.chemical_compound chemistry Nucleophile Thioglycosides Lectins Thiol Glycosyl |
| Zdroj: | Carbohydrate Research. 511:108481 |
| ISSN: | 0008-6215 |
| Popis: | In this work, we report the first synthesis of fluorinated thiodigalactoside analogues. We used tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the elaboration of two monofluorinated heterodimers, one difluorinated homodimer, and one difluorinated heterodimer. Moreover, we also present an alternative synthesis of 3-deoxy-3-fluorogalactose and 4-deoxy-4-fluorogalactose from a common precursor. Finally, this small set of more stable thiodigalactoside analogues could be interesting inhibitors of galactose-specific lectins. |
| Databáze: | OpenAIRE |
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