Selective N-Debenzylation of Benzylamino Derivatives of 1,6-Anhydro-β-d-hexopyranoses

When the series of 2-, 3-, and 4-(benzylamino)-2-, 3-, and 4-deoxy derivatives of 1,6-anhydro-β-d-hexopyranoses in the d-gluco, d-lyxo, and d-arabino configurations were reacted with diisopropyl azodicarboxylate, N-benzyl groups were selectively cleaved in the presence of O-benzyl groups. The yields ranged from 51 to 97%. The debenzylation of some aliphatic benzylamines is also discussed.