Synthetic mucin fragments: Synthesis of O-sulfo and O-methyl derivatives of allyl O-(β-D-galactopyranosyl)-(1 → 3)-2-acetamido-2-deoxy-α-D-galactopyranoside as potential compounds for sulfotransferases

Article abstract of DOI:10.1016/0008-6215(95)00162-M

Allyl 2-acetamido-4,6-O-(4-methoxybenzylidene)-2-deoxy-α-D-galactopyranosid e (1) was condensed with either 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (2) or 2,3,4-tri-O-benzoyl-6-O-bromoacetyl-α-D-galactopyranosyl bromide (14) in the presence of mercuric cyanide. Selective substitution with methyl, sulfo or both at desired positions, followed by the removal of protecting groups, afforded allyl O-(β-D-galactopyranosyl)-(1 → 3)-2-acetamido-2-deoxy-6-O-methyl-α-D-galactopyranoside (5), allyl O-(6-O-sulfo-β-D-galactopyranosyl sodium salt)-(1 → 3)2-acetamido-2-deoxy-6-O-methyl-α-D-galactopyranoside (10), allyl O-(β-D-galactopyranosyl)-(1 → 3)-2-acetamido-2-deoxy-6-O-sulfo-α-D-galactopyranoside sodium salt (13), allyl O-(6-O-sulfo-β-D-galactopyranosyl sodium salt)-(1 → 3)-2-acetamido-2-deoxy-α-D-galactopyranoside (17) and allyl O-(3-O-sulfo-β-D-galactopyranosyl sodium salt)-(1 → 3)-2-acetamido-2-deoxy-α-D-galactopyranoside (22). The structures of compounds 5, 10, 13, 17 and 22 were established by ¹³C NMR and FAB mass spectroscopy.