Selective N-debenzylation of benzylamino derivatives of 1, 6-anhydro-beta-D-hexopyranoses

J Kroutil; T Trnka; M Cerny

doi:10.1021/ol005746g

Selective N-debenzylation of benzylamino derivatives of 1, 6-anhydro-beta-D-hexopyranoses

Org Lett. 2000 Jun 15;2(12):1681-3. doi: 10.1021/ol005746g.

Authors

J Kroutil¹, T Trnka, M Cerny

Affiliation

¹ Department of Organic Chemistry, Charles University, Albertov 6, 128 43 Prague 2, Czech Republic.

PMID: 10880200
DOI: 10.1021/ol005746g

Abstract

When the series of 2-, 3-, and 4-(benzylamino)-2-, 3-, and 4-deoxy derivatives of 1,6-anhydro-beta-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.