Imidazole Promoted Efficient Anomerization of β-D-Glucose Pentaacetate in Solid State and Reaction Mechanism



Anomerization of glycosides was rarely performed under basic condition. Here an imidazole promoted anomerization of β-D-glucose pentaacetate in solid state at room temperature was discovered. This unprecedent anomerization in solid state occurred after simple mixing and reaction proceeded continuously to full conversion without stirring or mechanomixing. Current understanding of reaction mechanism involved with inter/intramolecular acyl transfer promoted by two imidazole in concerted manner may promote discovery of more new transformations of glucosides in solid state.

Version notes

Deleting some of discussions on the solution chemistry and adding new data and new discussion on solid state chemistry. A few new data was also added.


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Supplementary material

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supporting information
All reaction procedures, H NMR data, spectrum were included.