Zweifel olefination for C-glycosylation
Abstract C-glycosides are significant in medicinal chemistry due to their resistance to enzymatic hydrolysis, making them more stable and bioavailable compared to O-glycosides. Their unique structure also offers potential for developing drugs with improved therapeutic properties, particularly in tre...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2024-12-01
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| Series: | Communications Chemistry |
| Online Access: | https://doi.org/10.1038/s42004-024-01339-4 |
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| author | Florian Trauner Bilel Boutet Fabian Pilz Verena Weber Dorian Didier |
| author_facet | Florian Trauner Bilel Boutet Fabian Pilz Verena Weber Dorian Didier |
| author_sort | Florian Trauner |
| collection | DOAJ |
| description | Abstract C-glycosides are significant in medicinal chemistry due to their resistance to enzymatic hydrolysis, making them more stable and bioavailable compared to O-glycosides. Their unique structure also offers potential for developing drugs with improved therapeutic properties, particularly in treating diseases like diabetes and cancer. The main challenge in synthesizing C-glycosides lies in forming the carbon-carbon bond between the sugar and aglycone efficiently, while controlling the stereochemistry and minimizing side reactions. Starting from glycal derivatives, the Zweifel olefination presents an elegant opportunity to access C-glycosides in a selective manner. α-Lithiation of D-glucal, L-rhamnal, D-xylal and L-arabinal scaffolds was employed as a starting point in the synthesis of corresponding unsaturated aryl-, heteroaryl- and alkenyl-C-glycosides. This provides a straightforward strategy towards pharmacorelevant gliflozins and other unreported rhamnal- and xylal-analogs. |
| format | Article |
| id | doaj-art-72ffa0b14dcc496aaba5b0f1912dd9f4 |
| institution | Kabale University |
| issn | 2399-3669 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Communications Chemistry |
| spelling | doaj-art-72ffa0b14dcc496aaba5b0f1912dd9f42024-12-22T12:19:56ZengNature PortfolioCommunications Chemistry2399-36692024-12-017111010.1038/s42004-024-01339-4Zweifel olefination for C-glycosylationFlorian Trauner0Bilel Boutet1Fabian Pilz2Verena Weber3Dorian Didier4Technische Universität Darmstadt, Clemens-Schöpf-Institut für Organische Chemie und BiochemieTechnische Universität Darmstadt, Clemens-Schöpf-Institut für Organische Chemie und BiochemieLudwig-Maximillians Universität, Department ChemieInstitute for Neuroscience and Medicine and Institute for Advanced Simulations (INM-9/IAS-5), Computational Biomedicine, Forschungszentrum JülichTechnische Universität Darmstadt, Clemens-Schöpf-Institut für Organische Chemie und BiochemieAbstract C-glycosides are significant in medicinal chemistry due to their resistance to enzymatic hydrolysis, making them more stable and bioavailable compared to O-glycosides. Their unique structure also offers potential for developing drugs with improved therapeutic properties, particularly in treating diseases like diabetes and cancer. The main challenge in synthesizing C-glycosides lies in forming the carbon-carbon bond between the sugar and aglycone efficiently, while controlling the stereochemistry and minimizing side reactions. Starting from glycal derivatives, the Zweifel olefination presents an elegant opportunity to access C-glycosides in a selective manner. α-Lithiation of D-glucal, L-rhamnal, D-xylal and L-arabinal scaffolds was employed as a starting point in the synthesis of corresponding unsaturated aryl-, heteroaryl- and alkenyl-C-glycosides. This provides a straightforward strategy towards pharmacorelevant gliflozins and other unreported rhamnal- and xylal-analogs.https://doi.org/10.1038/s42004-024-01339-4 |
| spellingShingle | Florian Trauner Bilel Boutet Fabian Pilz Verena Weber Dorian Didier Zweifel olefination for C-glycosylation Communications Chemistry |
| title | Zweifel olefination for C-glycosylation |
| title_full | Zweifel olefination for C-glycosylation |
| title_fullStr | Zweifel olefination for C-glycosylation |
| title_full_unstemmed | Zweifel olefination for C-glycosylation |
| title_short | Zweifel olefination for C-glycosylation |
| title_sort | zweifel olefination for c glycosylation |
| url | https://doi.org/10.1038/s42004-024-01339-4 |
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