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

Add time:08/06/2019    Source:sciencedirect.com

The title compounds were prepared via the acetylated 2-bromoethyl glycoside 11 of α-d-Gal-(1→4)-β-d-Gal-(1→4)-β-d-Glc by displacement of bromide ion with methyl 3-mercaptopropionate, octadecanethiol, and hydrogen, respectively. Silver triflate-promoted glycosylation of 2-bromoethyl 2,3,6-tri-O-benzyl-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 11. A tetradeuterated analogue of 11 was prepared by essentially the same route. The spacer-arm glycoside formed from methyl 3-mercaptopropionate was coupled to bovine serum albumin and keyhole limpet haemocyanin.

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