SYNTHESES OF (α2-9) AND (α2-8) LINKED NEURAMINYLNEURAMINIC ACID DERIVATIVES

Article abstract of DOI:10.1016/S0040-4039(00)85176-X

A newly prepared glycosyl donor, the acetyl protected 2β-bromo-3β-hydroxy-N-acetylneuraminic ester was condensed with the protected 2-deoxy-2,3-dehydroneuraminic ester having a free hydroxy group at 9- or 8-position to form NeuAc(α2-9)NeuAc and NeuAc(α2-8)NeuAc linkage, respectively, which are involved in the group C meningococcal polysaccharides and gangliosides.The obtained 3β-hydroxy disaccharides were phenoxythiocarbonylated, reduced with tri-n-butylstannane, and deprotected to give the free glycosides in high yields.