Delineating the physical organic profile of the 6-fluoro glycosyl donor

• Anomeric-selectivity data was obtained for the 6-F and 6-OBn glucose donor scaffolds.
• At low temperatures the 6-OBn substitution increasingly outperformed the 6-F motif.
• Prevalence of the β-anomer was found with iPrOH as glycosyl acceptor.
• Eyring plots were constructed to derive the thermodynamic parametersΔΔH‡ andΔΔS‡.
• ΔΔS‡(6-F) ≈ ΔΔS‡(6-OBn) indicated similar rigidification of the β-transition states.

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