Synthesis and hydrolytic stability of the α and β anomers of 4′-thio-2′-deoxyuridine and their 5-substituted analogs. Competition between the acid-catalysed …

…, MI Elzagheid, GD Jones, AC MacCulloch…

Index: Otter, Graham P.; Elzagheid, Mohamed I.; Jones, Garry D.; MacCulloch, Alasdair C.; Walker, Richard T.; Oivanen, Mikko; Klika, Karel D. Journal of the Chemical Society. Perkin Transactions 2, 1998 , # 11 p. 2343 - 2349

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Citation Number: 11

Abstract

The α and β 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 ...