This study explores the switchable reactivity of glycals under controlled reaction conditions to access structurally diverse 3-oxo-glycals and 2-deoxy lactones. This switchable reactivity highlights the synthetic versatility of glycals and provides efficient routes to bioactive carbohydrate scaffolds with potential medicinal relevance.

Abstract

The switchable reactivity of glycals has been demonstrated by the successful synthesis of 3-oxo glycals and 2-deoxy lactones directly from glycals under ambient conditions. 3-Oxo glycals were obtained from various glycals via C3-oxidation employing (NH₄)₂S₂O₈ as an oxidant in DMSO solvent at 55 °C. However, 2-deoxy lactones were synthesized through C-1 oxidation using Pd(OAc)₂ as a catalyst and K₂S₂O₈ as an oxidant in the DMSO:H₂O solvent system. The methodology is operationally simple, high-yielding, scalable, and endowed with varied substrate scope.