Synthesis of spacer-arm, lipid, and ethyl glycosides of the terminal trisaccharide [α-d

Add time:08/07/2019    Source:sciencedirect.com

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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