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首页> 外文期刊>Acta Poloniae Pharmaceutica: Durg Research >Application of different α-1-thioglycosides preparation methods in synthesis of 5-nitro-2-pyridyl 1-thioglycosides - Substrates in synthesis of conjugates with uridine moiety. Part I
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Application of different α-1-thioglycosides preparation methods in synthesis of 5-nitro-2-pyridyl 1-thioglycosides - Substrates in synthesis of conjugates with uridine moiety. Part I

机译：不同的α-1-硫代糖苷制备方法在合成5-硝基-2-吡啶基1-硫代糖苷中的应用-底物在合成具有尿苷部分的结合物中。第一部分

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摘要

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 α-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.
机译：介绍了（5-硝基-2-吡啶基）2-脱氧-1-硫代糖苷的合成。获得的化合物用于合成尿苷衍生物，潜在的糖基转移酶抑制剂。在研究的第一阶段，将2-脱氧葡萄糖和2-脱氧半乳糖通过α-1-硫糖苷键与糖苷配基（硝基吡啶衍生物）相连。因此，在催化剂存在下，用2-硫代-5-硝基吡啶处理受保护的1，2-不饱和D-葡萄糖或D-半乳糖衍生物。在下一步中，通过使用乙酸中的锌粉，反应中的糖苷配基中的硝基被还原。然后，通过具有或不具有琥珀酸间隔基的酰胺键将这些化合物连接至选择性保护的尿苷衍生物。所获得的糖缀合物的不同之处在于碳水化合物部分的保护基以及糖和尿苷部分之间存在间隔基。

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