Improved Procedure for the Selective N-Debenzylation of Benzylamines by Diisopropyl Azodicarboxylate

The selective deprotection of N-benzyl group was achieved in the presence of azido, O-benzyl, and N-tosyl groups in reactions of benzylamines derived from 1,6-anhydro-β-d-glucopyranose with diisopropyl azodicarboxylate (DIAD) in THF. The key role of this solvent and the reaction pathway are presented together with proven reaction intermediates.