Abstract
The title compounds were prepared via the acetylated 2-bromoethyl β-glycoside ( 5) of α- d-Gal-(1→4)-β- d-Gal-(1→4)-β- d-GlcNAc by displacement of bromide ion with methyl 3-mercaptopropionate, octadecanethiol, and hydrogen, respectively. Silver triflate-promoted glycosylation of 2-bromoethyl 3,6-di- O-benzyl-2-deoxy-2-phthalimido-β- d-glucopyranoside with 2,3,6-tri- O-acetyl-4- O-(2,3,4,6-tetra- O-acetyl-α- d-galactopyranosyl)-α- d-galactopyranosyl bromide gave 5. The spacer-arm glycoside derived from methyl 3-mercaptoproprionate was coupled to bovine serum albumin and key-hole limpet haemocyanin to give neo-glycoproteins.
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