Creating glycoside diversity through stereoselective carboboration of glycals
Abstract Site-specific modification of glycosides to enhance or alter the physiological properties of the parent molecule has become a highly attractive strategy in drug development. However, creating glycoside building blocks with multiple diversifiable positions from readily available sugar precur...
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| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Nature Portfolio
2024-11-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-54016-4 |
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| Summary: | Abstract Site-specific modification of glycosides to enhance or alter the physiological properties of the parent molecule has become a highly attractive strategy in drug development. However, creating glycoside building blocks with multiple diversifiable positions from readily available sugar precursors remains a challenging task. Herein, we present a highly regio- and stereoselective nickel-catalyzed carboboration of glycals, which offers a platform for generating glycoside diversity with diverse C1 and C2 modification potential. Specially, the integration of a readily modifiable boronate group at the C2 position markedly amplifies the versatility of this approach, furnishing a universal method for swiftly generating diverse rare sugars with C2-site modifications through expedited downstream transformations. This method demonstrates a broad substrate scope and tolerates various functional groups and complex natural or drug molecular architectures. Moreover, we illustrate the synthetic potential of this method through the synthesis of a diverse array of analogs of both natural products and pharmaceuticals. |
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| ISSN: | 2041-1723 |