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The generation and fate of 2I-VII,3I-VII,6II-VII-icosa- O-methyl-β-cyclomaltoheptaos-6I- 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… Click to show full abstract
The generation and fate of 2I-VII,3I-VII,6II-VII-icosa- O-methyl-β-cyclomaltoheptaos-6I- 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 5VIIC. The radical can reach the anomeric hydrogen at 1VC 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 5VIIC, 2VIC, and 4VIC to obtain β-CD with a β-l-Ido p unit, acyclic hepta-, and hexa-saccharide structures, respectively.
Journal Title: Organic letters
Year Published: 2018
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