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

Full Text: HTML

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 ...

Related Articles:

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. Tetrahedron Letters, 1994 , vol. 35, # 41 p. 7569 - 7572]

Syntheses and antitumor activities of d-and l-2′-deoxy-4′-thio pyrimidine nucleosides

[Uenishi; Takahashi; Motoyama; Akashi; Sasaki Nucleosides and Nucleotides, 1994 , vol. 13, # 6-7 p. 1347 - 1361]

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. Tetrahedron Letters, 1994 , vol. 35, # 41 p. 7569 - 7572]

More Articles...