Synthesis of α-c(1 ← 3)-mannopyranoside of N-acetylgalactosamine, a new β-galactosidase inhibitor

Article abstract of DOI:10.1016/S0960-894X(99)00064-5

Radical C-glycosidation of a 3-methylidene-7-oxabicyclo[2.2.1]heptan-2- one derivative with acetobromomannose gave a α-C-mannopyranoside that was converted into α-D-ManpCH₂(1 ← 3)-D-GalNAc, a C-disaccharide that inhibits β-galactosidase from jack bean with IC₅₀ = 9.4 μM and K(i) = 7.5 μM (mixed mode of inhibition).