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

• Kesatebrhan Haile Asressu and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2019, 15, 2990–2999, doi:10.3762/bjoc.15.295

• 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. Keywords: acetolysis; acetolysis products; 2,7-anhydrosialic acid; SnCl4; Introduction Sialic acids are the most prevalent monosaccharides that are found at the nonreducing ends of glycans, and they are involved in many biologically important ligand–receptor interactions [1

• backbone of Neu5Ac. Thus, the aim of this study was to cleave the ring of the 2,7-anhydro derivatives with a choice of suitable Lewis acids as catalysts in order to utilize the acetolysis products as building blocks for the chemical synthesis of Neu5Ac-containing glycans. Results and Discussion It is known