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November 1, 1984Angewandte Chemie International Edition in English183 citations

Conformation of Glycosyl Radicals: Radical Stabilization by β‐CO Bonds

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JDJacques DupuisBGBernd GieseDRDaniel Rüegge

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Abstract

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.

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Cite This Study

Dupuis et al. (1984) studied this question.

synapsesocial.com/papers/6a1e5a5a1af840ad21409794https://doi.org/10.1002/anie.198408961
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