Concise synthesis of 2,7-anhydrosialic acid derivatives and its application

Add time:09/05/2019    Source:sciencedirect.com

In N-acetylneuraminic acid, apart from O9 and O8, a possible glycosylation site is the O4 position. For example, gangliosides HLG-2 and HPG-7 are considered to be potential lead compounds for carbohydrate-based drug development to treat neural disorders. However, the construction of their α(1 → 4) fucosyl sialic acid and α(2 → 4) linkages between sialic acids is difficult because of the regioselectivity problem. Herein, N-acetyl-2,7-anhydroneuraminic acid was synthesized in three steps from Neu5Ac methyl ester through per-O-trimethylsilylation, heating-assisted intramolecular anomeric protection (iMAP) and desilylation. The iMAP simultaneously circumvents both the 2- and 7-OH protection. Upon protecting the 8- and 9-OH groups as a benzylidene acetal, only 4-OH is free for glycosylation. These 2,7-anhydro-8,9-O-benzylidenesialic acid derivatives were examined as acceptor for an α-selective fucosylation to construct the glycosidic linkage of fucosyl α(1 → 4) 2,7-anhydroneuraminic acid.

We also recommend Trading Suppliers and Manufacturers of 8-O-acetyl-N-acetylneuraminic acid (cas 18529-64-1). Pls Click Website Link as below: cas 18529-64-1 suppliers

Prev:Observation of ψ(3686)→η′e+e−
Next:Sialic acids in the extracellular polymeric substances of seawater-adapted aerobic granular sludge)