Tetrahedron p. 1291 - 1298 (1988)
Update date:2022-09-26
Topics: Glycosidic Bond Formation Deprotection of Hydroxyl Groups
Okamoto, Kaoru
Kondo, Tadao
Goto, Toshio
NeuAc(α2-9)NeuAc and NeuAc(α2-8)NeuAc disaccharides, 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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