SnCl4-catalyzed Solvent-free Acetolysis of 2,7-Anhydrosialic Acid Derivatives

Submitting author affiliation:
Academia Sinica, Taipei, Taiwan, Province of China

Beilstein Arch. 2019, 2019131.

Published 25 Oct 2019



Sialic acid-containing glycans are found in different sialic acid forms and a variety of glycosidic linkages in biologically active glycoconjugates. Hence, the preparation of suitably protected sialyl building blocks requires high attention in order to access glycans in pure form. In this line, various C-5 substituted 2,7-anhydrosialic acid derivatives bearing both electron donating and withdrawing protecting groups were synthesized and subjected to different Lewis acid-catalyzed solvent free ring opening reactions at room temperature in the presence of acetic anhydride. Among the various Lewis acids tested, the desired acetolysized products were obtained in moderate yields under a tin(IV) chloride catalysis system. Our methodology can be extended to regioselective protecting group installation and manipulation towards a number of thiosialoside and halide donors.

Keywords: Keywords: acetolysis; acetolysized products; 2,7-anhydrosialic acid; SnCl4

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Asressu, K. H.; Wang, C.-C. Beilstein Arch. 2019, 2019131. doi:10.3762/bxiv.2019.131.v1

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