Reductive Radical Cascades Triggered by Alkoxyl Radicals in the β-Cyclodextrin Framework
The generation and fate of 2,3,6-icosa-O-methyl-β-cyclomaltoheptaos-6-O-yl radical under reductive conditions is described. Two radical cascade reactions are involved: the main one is triggered by a 1,8-HAT of the hydrogen at 5C. The radical can reach the anomeric hydrogen at 1C three sugar units ahead using a six-step sequence. The different hydrogen donor ability of the group 14 hydrides permits one to selectively stop the cascade at 5C, 2C, and 4C to obtain β-CD with a β-l-Idop unit, acyclic hepta-, and hexa-saccharide structures, respectively.
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| Main Authors: | , , , |
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| Other Authors: | |
| Format: | artículo biblioteca |
| Published: |
American Chemical Society
2018-05-16
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| Subjects: | Alkoxyl radicals, Cyclodextrin, Reductive radical cascades, |
| Online Access: | http://hdl.handle.net/10261/181447 http://dx.doi.org/10.13039/100012000 http://dx.doi.org/10.13039/501100003329 |
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| Summary: | The generation and fate of 2,3,6-icosa-O-methyl-β-cyclomaltoheptaos-6-O-yl radical under reductive conditions is described. Two radical cascade reactions are involved: the main one is triggered by a 1,8-HAT of the hydrogen at 5C. The radical can reach the anomeric hydrogen at 1C three sugar units ahead using a six-step sequence. The different hydrogen donor ability of the group 14 hydrides permits one to selectively stop the cascade at 5C, 2C, and 4C to obtain β-CD with a β-l-Idop unit, acyclic hepta-, and hexa-saccharide structures, respectively. |
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