Syntheses of (α2–9) and (α2–8) linked neuraminylneuraminic acid derivatives

✍ Scribed by Kaoru Okamoto; Tadao Kondo; Toshio Goto

• Book ID: 104219255
• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 239 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)85176-x

✦ Synopsis

A newly prepared glycosyl donor, the acetyl protected 2&bromo-3B-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(aZ-9)NeuAc and NeuAc(aZ-8)-NeuAc linkage, respectively, which are involved in the group C meningococcal polysaccharides and gangliosides.

The obtained 38hydroxy disaccharides were phenoxythiocarbonylated, reduced with tri-n-butylstannane, and deprotected to give the free glycosides in high yields.