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

Authors
Kroutil, J Trnka, T Cerny, M
Citation
J. Kroutil et al., Selective N-debenzylation of benzylamino derivatives of 1,6-anhydro-beta-d-hexopyranoses, ORG LETT, 2(12), 2000, pp. 1681-1683
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
12
Year of publication
2000
Pages
1681 - 1683
Database
ISI
SICI code
1523-7060(20000615)2:12<1681:SNOBDO>2.0.ZU;2-T
Abstract
[GRAPHICS] When the series of 2-, 3-, and 4-(benzylamino)-2-, 3-, and 4-deoxy derivati ves of 1,6-anhydro-beta-D-hexopyranoses in the D-gluco D-lyxo, and D-arabin o configurations were reacted with diisopropyl azodicarboxylate, N-benzyl g roups were selectively cleaved in the presence of O-benzyl groups. The yiel ds ranged from 51 to 97%, The debenzylation of some aliphatic benzylamines is also discussed.