109714-18-3

Upstream product

• 109681-08-5 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranosonate 
• 108999-11-7 methyl 5-acetamido-4,7,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enopyranosonate 
• 109681-19-8 methyl 5-acetamido-4,7,9-tri-O-acetyl-2,6-anhydro-2,3,5-trideoxy-8-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-β-D-erythro-L-gluco-2-nonulopyranosylonate)-D-glycero-D-galacto-non-2-enopyranosonate 
• 1005-56-7 phenylcarbonochloridothioate 

Relevant academic research and scientific papers

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 ESTER

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.

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

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.