Circular dichroism and anomeric configuration assignment of benzimidazole C-nucleoside analogs.

The circular dichroism of a series of acyclic polyhydroxyalkyl benzimidazole C-nucleoside analogs was correlated with the stereochemistry of the chiral carbon atom α to the benzimidazole base moiety. This correlation was used for the assignment of the anomeric configuration of 2-(β-l-erythrofuranosyl) benzimidazole C-nucleoside analogs without a need to have the other anomer on hand, in a similar manner to the correlation obtained for assignment of the anomeric configuration of triazole C-nucleoside analogs.