Nucleosides, Nucleotides and Nucleic Acids

Ring-Opening of 3-β-D-Ribofuranosyl-3, 7, 8, 9-Tetrahydropyrimido [1, 2-i] Purin-8-ol and Preparation of 2-Thio-and 2-aza-Adenosine Derivatives

P Sund, L Kronberg

Index: Sund, Pernilla; Kronberg, Leif Nucleosides, Nucleotides and Nucleic Acids, 2008 , vol. 27, # 12 p. 1215 - 1226

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Citation Number: 2

Abstract

The adduct 3-β-D-ribofuranosyl-3, 7, 8, 9-tetrahydropyrimido [1, 2-i] purin-8-ol (2), obtained from adenosine and epichlorohydrin, underwent ring fission at basic conditions. The initial ring-opening took place at C2 of the pyrimidine unit resulting in 2-(5-amino-1-β-D- ribofuranosyl-imidazol-4-yl)-1, 4, 5, 6-tetrahydropyrimidin-5-ol (3). Also the tetrahydropyrimidine ring of 3 could be opened resulting in 5-amino-1-(β-D-ribofuranosyl)- ...