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A transformation from the chair- into the boat conformation takes place when glucosides such as 1 are converted into glucosyl radicals 2. This preference for the boat conformation is due to the radical-stabilizing effect of the coplanar arrangement of the β-CO bond and semi-occupied orbital. The findings are of interest regarding stereoselective radical CC-linkage in the synthesis of C-glycosides.
Dupuis et al. (Thu,) studied this question.
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