Radical mediated synthesis of N-acetyl-D-galactosamine containing C-disaccharides via a temporary phosphoramidic connection

Article abstract of DOI:10.1016/S0957-4166(97)00141-9

The C-disaccharide {α-D-GalNAc-C-(1→4)-β-D-Glc-OMe} and its interglycosidic β anomer were synthesized by radical coupling of phenyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside onto methyl 2,6-di-O-benzyl-4-deoxy-4-C-methylene- β-D-xylo-hexopyranoside, which are temporarily connected through a phosphoramido tether. A similar reaction was performed with methyl 2,3-di-O-benzyl-4-deoxy-4-C-methylene-α-D-xylo-hexopyranoside to produce the two closely related α-OMe C-disaccharides.