Synthesis of iodobenzylidene and iodoethylidene acetals of d-glucose

Abstract

The synthesis of two iodinated acetals of d-glucose, analogues of d-glucose acetals which are known to interact with the glucose transport protein GluT, is presented. The iodobenzylidene acetal was obtained by acetalation of 1,2,3-tri- O-acetyl-d-glucopyranose, whereas the iodoethylidene acetal was prepared from the corresponding prop-2-enylidene derivative by an ozonation/reduction sequence, followed by iodination of the resulting hydroxyethylidene derivative. These two iodinated acetals have been prepared towards studies of the transport of d-glucose by SPECT.