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首页> 外文期刊>Journal of the Chemical Society. Perkin Transactions 2 >Synthesis and hydrolytic stability of the alpha and beta anomers of 4 '-thio-2 '-deoxyuridine and their 5-substituted analogs. Competition between the acid-catalysed depyrimidination and isomerisation to a 5-thiopyranoside nucleoside
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Synthesis and hydrolytic stability of the alpha and beta anomers of 4 '-thio-2 '-deoxyuridine and their 5-substituted analogs. Competition between the acid-catalysed depyrimidination and isomerisation to a 5-thiopyranoside nucleoside

机译：4'-硫代-2'-脱氧尿苷及其5取代类似物的α和β端基异构体的合成和水解稳定性。酸催化去嘧啶化和异构化为5-硫代吡喃糖苷核苷之间的竞争

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摘要

The alpha and beta anomers of 4'-thio-2'-deoxyuridine were readily synthesised as an anomeric mixture using adapted methodology and separated chromatographically as their 3',5'-di-O-benzyl-N-3-benzoyl derivatives. The 5-fluoro analogs were prepared in a similar manner, but the anomers could be separated simply as their 3',5'-di-O-benzyl derivatives. The kinetics of acid-catalysed hydrolysis for the four compounds and their 5-alkylated analogs are reported. Under these conditions, cleavage of the N-glycosidic bond competes with the reversible isomerisation between the furano (4'-thio) and pyrano (5'-thio) ring systems. This was confirmed by isolation and NMR characterisation of the alpha and beta pyranose intermediates of the parent compounds. [References: 18]
机译：4'-硫代-2'-脱氧尿苷的α和β端基异构体易于使用适应性方法合成为异头混合物，并色谱分离为其3'，5'-二-O-苄基-N-3-苯甲酰基衍生物。以类似的方式制备5-氟类似物，但可以将它们的3'，5'-二-O-苄基衍生物简单地分离出来。报道了四种化合物及其5-烷基化类似物的酸催化水解动力学。在这些条件下，N-糖苷键的断裂与呋喃（4'-硫基）和吡喃（5'-硫基）环系统之间的可逆异构化竞争。通过母体化合物的α和β吡喃糖中间体的分离和NMR表征证实了这一点。 [参考：18]

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