Stereoselective synthesis of α-L-Fucp-(1,2)- and -(1,3)-β-D-Galp(1)-4-methylumbelliferone using glycosyl donor substituted by propane-1,3-diyl phosphate as leaving group

Article abstract of DOI:10.1039/b002754p

Stereoselective synthesis of α-L-Fucp-(1,2)- and -(1,3)-β-D-Galp(1)-4-methyllumbelliferone was accomplished using glycosyl donor substituted by propane-1,3-diyl phosphate as leaving group. The α-stereochemistry for the anomeric centre was assigned on the basis of the observed ¹³C-H coupling constant of 165.4 Hz for the bond. The results suggested that the bond-forming reaction intermediate was formed through participation of the second carbon acetoxy function or by an S_N2-like process.