200481-27-2Relevant academic research and scientific papers
Synthesis of aminopropylglycoside of the SiaTn antigen Neu5Acα2-6GalNAcα
Simeoni,Byramova,Bovin
, p. 683 - 691 (2007/10/03)
The synthesis of the SiaTn disaccharide, hapten of a tumor-associated antigen, as a derivative convenient for condensation with a polymer carrier was described. Selective sialylation of the primary hydroxyl group in (3-trifluoroacetamidopropyl)-2-azido-2-deoxy-α-D-galactopyranoside with a derivative of ethylthioglycoside of N-acetylneiraminic acid promoted with N-iodosuccinimide-trifluoromethanesulfonic acid (or its trimethylsilyl ester) pair provided α2 → 6- and β2 → 6-sialylgalactosides with 41 and 23% yields, respectively. Catalytic hydrogenolysis of the azido group, N-acetylation, and subsequent O- and N-deacetylation provided the target aminopropylglycoside Neu5Acα2-6GalNAcα1-O(CH2)3NH2. The use of 3,4-O-isopropylidene derivative with the only free C6 hydroxyl group as a glycosyl acceptor shifted stereoselectivity of the sialylation towards the formation of the β-disaccharide.
