Tetrahedron Letters p. 5229 - 5232 (1986)
Update date:2022-08-03
Topics:
Okamoto, Kaoru
Kondo, Tadao
Goto, Toshio
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.
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