Syntheses of (α2–9) and (α2–8) linked dineuraminyl saccharides by use of 2β-bromo-3β-hydroxy-4,7,8,9-tetra-o-acetyl-n-acetylneuraminic acid methyl ester1

Add time:09/08/2019    Source:sciencedirect.com

NeuAc(α2–9)NeuAc and NeuAc(α2–8)NeuAc disacchrides, which are involved in the group C meningococcal polysaccharides and gangliosides, were synthesized by condensation of the acetyl protected 2-deoxy-2,3-dehydroneuraminic acid methyl ester having a hydroxyl group at 9 or 8 position with the acetyl protected 2β-bromo-3β-hydroxy-N-acetylneuraminic ester in preference to the corresponding β-glycosides. The hydroxyl groups of the obtained glycosides were removed by phenoxythiocarbonylation followed by reduction with tributylstannane and the resultant disaccharides were deprotected to afford the free glycosides in good yields.

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