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
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
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.