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The generation and fate of 2 I-VII ,3 I-VII ,6 II-VII -icosa- O-methyl-β-cyclomaltoheptaos-6 I - 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 5 VII C. The radical can reach the anomeric hydrogen at 1 V C 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 5 VII C, 2 VI C, and 4 VI C to obtain β-CD with a β-l-Ido p unit, acyclic hepta-, and hexa-saccharide structures, respectively.

Reductive Radical Cascades Triggered by Alkoxyl Radicals in the β-Cyclodextrin Framework