Stereoselective synthesis of alpha-L-Fucp-(1,2)- and -(1,3)-beta-D-Galp(1)-4-methylumbelliferone using glycosyl donor substituted by propane-1,3-diylphosphate as leaving group

Citation
H. Vankayalapati et G. Singh, Stereoselective synthesis of alpha-L-Fucp-(1,2)- and -(1,3)-beta-D-Galp(1)-4-methylumbelliferone using glycosyl donor substituted by propane-1,3-diylphosphate as leaving group, J CHEM S P1, (14), 2000, pp. 2187-2193
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14704358 → ACNP
Issue
14
Year of publication
2000
Pages
2187 - 2193
Database
ISI
SICI code
1470-4358(2000):14<2187:SSOAA->2.0.ZU;2-1
Abstract
The synthesis of the disaccharides alpha-L-Fucp-(1,2)- and alpha-L-Fucp-(1, 3)-beta-D-Galp(1)-4-methylumbelliferone as fucosidase substrates was accomp lished by activation of the anomeric centre of 2,3,4-tri-O-acetyl- and 2,3, 4,6-tetra-O-acetyl-alpha,beta-L-fuco- and -D-galactopyranosyl propane-1,3-d iyl phosphates with TMSOTf and with minimal protection of 4-methylumbellife ryl beta-D-galactopyranoside.