Alkylating agents from sugars. Stereoselective synthesis of 2,3-diaminoglucoses from 2-nitroalkenes, as intermediates in the synthesis of carriers ofchlorambucil

Authors
Vega-Perez, JM Candela, JI Blanco, E Iglesias-Guerra, P
Citation
Jm. Vega-perez et al., Alkylating agents from sugars. Stereoselective synthesis of 2,3-diaminoglucoses from 2-nitroalkenes, as intermediates in the synthesis of carriers ofchlorambucil, TETRAHEDRON, 55(31), 1999, pp. 9641-9650
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
31
Year of publication
1999
Pages
9641 - 9650
Database
ISI
SICI code
0040-4020(19990730)55:31<9641:AAFSSS>2.0.ZU;2-0
Abstract
The synthesis of alkyl 2,3-diamino and alkyl 2-amino-3-thioglucopyranosides from alkyl 2-nitrosugar derivatives and amines or thiols is described. The reaction takes place through a 2-nitroalkene in good yield and with high s tereoselectivity. The bonding of alkyl 2,3-diaminoglucopyranosides to chlor ambucil via a spacer arm and an ester function is also described. (C) 1999 Elsevier Science Ltd. All rights reserved.