134136-41-7

Upstream product

• 100-02-7 4-nitro-phenol 
• 113757-77-0 benzyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulpyranosid)onate 
• 100-39-0 benzyl bromide 
• 113757-76-9 (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(benzyloxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 
• 19342-36-0 2,4,7,8,9-Penta-O-acetyl-N-acetyl-β-D-neuraminsaeure 
• 824-78-2 4-nitrophenol sodium salt 

Downstream Products

• 59694-35-8 methyl <(4-nitrophenyl) 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid>onate 
• 134136-42-8 4-Aminophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didedoxy-α-D-glycero-D-galacto-2-nonulopyranosidonic acid 

Relevant academic research and scientific papers

A facile access to aryl α-sialosides: The combination of a volatile amine base and acetonitrile in glycosidation of sialosyl chlorides

We have succeeded in achieving a facile access to 4-nitrophenyl and 4-methylumbelliferyl-α-sialosides. To sialosyl chlorides which are fully protected with acetyl groups as glycosyl donors, the action of phenols with diisopropylethylamine in acetonitrile brought about high yield as well as facile product isolation.

Regioselective Acetylations of Sialic Acid α-Ketosides

Various partially acetylated sialic acid α-ketosides were obtained without expensive protecting group techniques by using trimethyl orthoacetate or dimethylacetamide dimethyl acetal as acetylating agents or by performing a partial Zemplen de-O-acetylation.Using trimethyl orthoacetate as acetylating agent, we synthesized 9-O-acetylated, 8-O-acetylated, and 8,9-di-O-acetylated sialic acid α-ketoside benzyl ester derivatives.The acetylation with dimethylacetamide dimethyl acetal yielded 9-O-acetylated, 8-O-acetylated, 4,9-di-O-acetylated, 8,9-di-O-acetylated, and 4,8,9-tri-O-acetylated sialic acid α-ketoside benzyl ester derivatives.The partial Zemplen de-O-acetylation permitted the synthesis of 7,8,9-tri-O-acetylated sialic acid α-ketoside benzyl ester derivatives.After catalytic hydrogenation the 8-O-acetylated derivatives 2e and 3d were not stable and were completely converted into the 9-O-acetylated sialic acid α-thioketoside 2k.The N-acetyl-8,9-di-O-acetylneuraminic acid α-aminophenylthioketoside 2l showed a migration of the acetyl group from position 8 to position 7 in polar solvents, yielding a mixture of the 8,9-di-O- and the 7,9-di-O-acetylated derivatives 2l and 2m in a molar ratio of approximately 1:1.The 7,9-di-O-acetylated derivative 2m could be separated and was completely stable in methanol.Using the isopropylidene protecting group we could also prepare the 4-O-acetylated sialic acid α-thioketoside 2o.Treatment of the 9-O-acetylated derivative 2k with fluorescein isothiocyanate gave the fluorescent derivative 5. - Key Words: Sialic acids / Thioketosides