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Synthesis of α- and β-Methyl NEU5Ac α-(2→8) NEU5Ac Disaccharides

1990; Taylor & Francis; Volume: 9; Issue: 6 Linguagem: Inglês

10.1080/07328309008543882

1532-2327

Safdar Abbas, Shigeo Sugiyama, James Diakur, Robert A. Pon, René Roy,

Bacterial Infections and Vaccines

ABSTRACT Acid hydrolysis of colominic acid, an α-(2→8)-linked oligomer of sialic acid, yielded Neu5Ac α-(2→8) Neu5Ac (di-Neu5Ac) 2 as one of the products. Starting from this disaccharide, it was possible to prepare two potential di-Neu5Ac donors, 5 and 8, as their corresponding 2-chloro derivatives. Subsequent reaction of the donor 8 with methanol as a simple acceptor led to the α- and β-methyl Neu5Ac α-(2→8) Neu5Ac glycosides.