Large Scale Synthesis of A Derivative of An α-Galactosyl Trisaccharide Epitope Involved in the Hyperacute Rejection of Xenotransplantation
- 1 January 1999
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 18 (8) , 1009-1017
- https://doi.org/10.1080/07328309908544050
Abstract
A derivative of an α-galactosyl trisaccharide xenoactive antigen, (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1→3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide (5), was synthesized on a large scale (50 gram). The synthesis involved a high yielding and highly stereoselective (α/β>20:1) glycosylation reaction utilizing a thiogalactoside as the donor and a selectively protected lactose azide as the acceptor. This derivative serves as a versatile intermediate that can be transformed into a variety of α-Gal containing glycoconjugates highly desired in xenotransplantation research and pharmaceutical development.Keywords
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