Starting from 1-deoxynojirimycin 1-sulfonic acid, 1-α-cyano-1-deoxynojirimycin can be prepared in 80% yield. Silylation of all the OH groups produces (1), which reacts with alkyl and aryl Grignard reagents in good yields with complete exchange of the CN group. 1-Deoxynojirimycin derivatives are pharmacologically effective as α-glucosidase inhibitors.
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Böshagen et al. (1981) studied this question.
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