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Acta poloniae pharmaceutica

Application of different alpha-1-thioglycosides preparation methods in synthesis of 5-nitro-2-pyridyl 1-thioglycosides substrates in synthesis of conjugates with uridine moiety. Part I.


PMID 23285688

Abstract

The synthesis of (5-nitro-2-pyridyl) 2-deoxy-1-thioglycosides is presented. Obtained compounds were used in the synthesis of uridine derivatives, potential glycosyltransferases inhibitors. In the first stage of the research 2-deoxyglucose and 2-deoxygalactose were connected to aglycone (nitropyridine derivative) via alpha-1-thioglycosidic bond. Therefore, protected 1.2-unsaturated D-glucose or D-galactose derivatives were treated with 2-thio-5-nitropyridine in the presence of the catalyst. In the next step nitro group in the aglycone was reduced in the reaction with the use of zinc dust in acetic acid. Then, these compounds were connected to selectively protected uridine derivatives by amide bond with or without succinic spacer. The obtained glycoconjugates differ in the protecting group of the carbohydrate part and in the presence of the spacer between the sugar and uridine moiety.