Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose
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·1H...
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Beilstein-Institut
2020-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.16.237 |
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doaj-600a449108ee4f15b50cba6d8a885b572021-04-02T16:28:40ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-11-011612880288710.3762/bjoc.16.2371860-5397-16-237Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranoseDanny Lainé0Vincent Denavit1Olivier Lessard2Laurie Carrier3Charles-Émile Fecteau4Paul A. Johnson5Denis Giguère6Département de chimie, Université Laval, 1045 av. De la Médecine, Québec City, Qc, G1V 0A6, CanadaDépartement de chimie, Université Laval, 1045 av. De la Médecine, Québec City, Qc, G1V 0A6, CanadaDépartement de chimie, Université Laval, 1045 av. De la Médecine, Québec City, Qc, G1V 0A6, CanadaDépartement de chimie, Université Laval, 1045 av. De la Médecine, Québec City, Qc, G1V 0A6, CanadaDépartement de chimie, Université Laval, 1045 av. De la Médecine, Québec City, Qc, G1V 0A6, CanadaDépartement de chimie, Université Laval, 1045 av. De la Médecine, Québec City, Qc, G1V 0A6, CanadaDépartement de chimie, Université Laval, 1045 av. De la Médecine, Québec City, Qc, G1V 0A6, CanadaIn 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.https://doi.org/10.3762/bjoc.16.237deoxyfluorinationet3n·3hffluorine effectpolyfluorinated carbohydratespolyfluoroalditol analogues |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Danny Lainé Vincent Denavit Olivier Lessard Laurie Carrier Charles-Émile Fecteau Paul A. Johnson Denis Giguère |
| spellingShingle |
Danny Lainé Vincent Denavit Olivier Lessard Laurie Carrier Charles-Émile Fecteau Paul A. Johnson Denis Giguère Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose Beilstein Journal of Organic Chemistry deoxyfluorination et3n·3hf fluorine effect polyfluorinated carbohydrates polyfluoroalditol analogues |
| author_facet |
Danny Lainé Vincent Denavit Olivier Lessard Laurie Carrier Charles-Émile Fecteau Paul A. Johnson Denis Giguère |
| author_sort |
Danny Lainé |
| title |
Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose |
| title_short |
Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose |
| title_full |
Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose |
| title_fullStr |
Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose |
| title_full_unstemmed |
Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose |
| title_sort |
fluorine effect in nucleophilic fluorination at c4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-d-hexopyranose |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2020-11-01 |
| description |
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. |
| topic |
deoxyfluorination et3n·3hf fluorine effect polyfluorinated carbohydrates polyfluoroalditol analogues |
| url |
https://doi.org/10.3762/bjoc.16.237 |
| work_keys_str_mv |
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