166813-00-9Relevant academic research and scientific papers
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 depyrimidination and isomerisation to a 5-thiopyranoside nucleoside
Otter, Graham P.,Elzagheid, Mohamed I.,Jones, Garry D.,MacCulloch, Alasdair C.,Walker, Richard T.,Oivanen, Mikko,Klika, Karel D.
, p. 2343 - 2349 (2007/10/03)
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-N3-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 α and β pyranose intermediates of the parent compounds.
Unanticipated retention of configuration in the DAST fluorination of deoxy-4′-thiopyrimidine nucleosides with "up" hydroxyl groups
Jeong, Lak S.,Nicklaus, Marc C.,George, Cliff,Marquez, Victor E.
, p. 7569 - 7572 (2007/10/02)
Fluorination of 1-(5-O-trityl-3-deoxy-4-thio-β-D-threo-pentofuranosyl)uracil (17) and 1-(5-O-trityl-2-deoxy-4-thio-β-D-threo- pentofuranosyl)uracil (20) with DAST proceeded with exclusive retention of configuration. The structures of the products were con
