Synthesis of the methyl glycosides of a tri- and a tetra-saccharide related to heparin and heparan sulphate

Article abstract of DOI:10.1016/0008-6215(93)84030-A

The methyl glycoside of a tetrasaccharide isolated from heparin, methyl O-(α-L-idopyranosyluronic acid)-(1 → 4)-O-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1 → 4)-O-(β-D-glucopyranosyluronic acid)-(1 → 3)-O-β-D-galactopyranoside disodium salt and a trisaccharide derivative thereof, methyl O-(α-L-idopyranosyluronic acid)-(1 → 4)-O-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1 → 4)-O-β-D-glucopyranosyluronic acid disodium salt, were synthesized using a block-type strategy. A suitable protected disaccharide block of iduronic acid and glucosamine (IdoA-GlcN) was used as a key intermediate for the syntheses and was glycosidated with a protected galactose derivative and a disaccharide block of glucuronic acid and galactose (GlcA-Gal) to give tri- and tetra-saccharide derivatives, respectively. Deprotection gave the target compounds. The methyl glycoside of a tetrasaccharide isolated from heparin, disodium salt and a trisaccharide derivative thereof, were synthesized using a block-type strategy. A suitable protected disaccharide block of iduronic acid and glucosamine (IdoA-GlcN) was used as a key intermediate for the syntheses and was glycosidated with a protected galactose derivative and a disaccharide block of glucuronic acid and galactose (GlcA-Gal) to give tri-and tetra-saccharide derivatives, respectively. Deprotection gave the target compounds.