5983-05-1Relevant academic research and scientific papers
5'-O-benzoyl-2'-keto-3'-deoxy-α-uridine: First unambiguous synthesis, crystal structure and its use to establish the anomerisation of 2'-ketouridines under basic conditions
Sakthivel, Kandasamy,Pathak, Tanmaya,Suresh, Cheravakkattu G.
, p. 1767 - 1772 (2007/10/03)
5'-O-benzoyl-3'-deoxy-2'-keto-α-uridine was characterised unambiguously with the help of crystal structure analysis and provided 1H-NMR data to differentiate it from its β-anomer. We have also established, with the help of the above 1H-NMR data that the earlier reported procedures of synthesising 2'-ketouridine produced a mixture of anomers.
Synthesis of 1-(3′-deoxy-β-D-glycero-pentofuran-2′-ulosyl)uracil by selective elimination reactions
Sasaki,Minamoto,Hattori
, p. 2689 - 2694 (2007/10/09)
For the synthesis of y 1-(3′-deoxy-β-D-glycero-pentofuran-2′-ulosyl)uracil (16), the precursor, 5′-O-benzoyl derivative (2),2 was elaborated in a variety of ways. 1-(5′-O-Benzoyl-3′-O-tosyl-β-D- lyxofuranosyl)uracil (4)2 was benzoylated to N3-benzoyl-1-(2′,5′-di-O-benzoyl-3′-O-tosyl-β-D- lyxofuranosyl)uracil (5), which directly yielded 2 on treatment with sodium benzoate. 1-(3′,5′-Di-O- benzoyl-2′-O-tosyl-β-D-lyxofuranosyl)uracil (8) and its 3′,5′-O-isopropylidene analog (10) resisted elimination reactions, thus proving absolute selectivity in the elimination of the derivatives of 1-β-D- lyxofuranosyl-uracil. Seeking a more economical path to 2, 1-(5′-O-benzoyl-β-D-lyxofuranosyl)uracil (11) was first benzoylated to give 2′,5′-di-O-benzoate (12), accompanied by 3′,5′-di- and 2′,3′,5′-tri-O- benzoate. Mesylation of the major product (12) gave 1-(2′,5′-di-O-benzoyl-3′-O-mesyl-β-D- lyxofuranosyl)uracil (15), which, on treatment with sodium benzoate, gave 2 in an highly improved yield. Basic hydrolysis on 2 gave compound 16.
