Potential anticancer drugs, 4 - Glycosyl glycerol derivatives as drug carrier system. Stereoselective synthesis of epoxyalkyl N-acyl-beta-D-glucopyranosides and their reactivity with nucleophiles

Citation
Jm. Vega-perez et al., Potential anticancer drugs, 4 - Glycosyl glycerol derivatives as drug carrier system. Stereoselective synthesis of epoxyalkyl N-acyl-beta-D-glucopyranosides and their reactivity with nucleophiles, EUR J ORG C, (23), 2000, pp. 3949-3956
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
23
Year of publication
2000
Pages
3949 - 3956
Database
ISI
SICI code
1434-193X(200012):23<3949:PAD4-G>2.0.ZU;2-H
Abstract
The synthesis of alkenyl 2-acylamino-4,6-O-benzylidene-2-deoxy-beta -D-gluc opyranosides from N-acetyl-D-glucosamine is described. The oxidation of alk enyl glycosides with m-CPBA gives the corresponding oxiranes in good yields , and with high stereoselectivity. Analogues of glycosyl glycerol derivativ es, which can be used as drug carriers, were obtained by various ring-openi ng reactions with different nitrogen, sulfur, and carbon nucleophiles.