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Stereoselective synthesis and conformational study of novel 2′,3′-didehydro-2′,3′-dideoxy-4′-selenonucleosides
- Stereoselective synthesis and conformational study of novel 2′,3′-didehydro-2′,3′-dideoxy-4′-selenonucleosides
- Tosh D.K.; Won J.C.; Hea O.K.; Lee Y.; Pal S.; Hou X.; Choi J.; Choi S.; Lak S.J.
- Ewha Authors
- 정낙신; 최선; 최원준
- SCOPUS Author ID
- Issue Date
- Journal Title
- Journal of Organic Chemistry
- vol. 73, no. 11, pp. 4259 - 4262
- SCI; SCIE; SCOPUS
- (Chemical Equation Presented) Stereoselective synthesis of novel 2′,3′-didehydro-2′,3′-dideoxy-4′- selenonucleosides (4′-seleno-d4Ns) 4a-c was accomplished via 4′-selenoribofuranosyl pyrimidines 11a-c, as key intermediates. 4′-Selenoribofuranosyl pyrimidines 11a-c were efficiently synthesized from D-ribose or D-gulonic γ-lactone using a Pummerer-type condensation as a key step. Introduction of 2′,3′-double bond was achieved by treating cyclic 2′,3′-thiocarbonate with 1,3-dimethyl-2-phenyl-1,3,2- diazaphospholidine. © 2008 American Chemical Society.
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