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SnCl4-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives.

ABSTRACT: 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 a pure form. In line with this, 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 acetolysis products were obtained in moderate yields under tin(IV) chloride catalysis. Our methodology could be extended to regioselective protecting group installations and manipulations towards a number of thiosialoside and halide donors.

SUBMITTER: Asressu KH

PROVIDER: S-EPMC6948141 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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SnCl<sub>4</sub>-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives.

Asressu Kesatebrhan Haile KH Wang Cheng-Chung CC

Beilstein journal of organic chemistry 20191223

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 a pure form. In line with this, 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 ...[more]

PMID: 31949543

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