82
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of 9-(2,3-Dideoxy-2,3-Difluoro-β-D- Arabinofuranosyl)Adenine

, &
Pages 1387-1389 | Published online: 05 Dec 2007

REFERENCES

  • Pankiewicz , K. W. 2000 . Fluorinated nucleosides . Carbohydr. Res. , 327 : 87 – 105 .
  • Sivets , G. G. , Kalinichenko , E. N. and Mikhailopulo , I. A. 2006 . Synthesis of C2′-β-fluoro-substituted adenine nucleosides via pivaloyl derivatives of adenosine and 3′-deoxyadenosine . Letters Org. Chem. , 5 : 402 – 408 .
  • Wright , J. A. , Taylor , N. F. and Fox , J. J. 1969 . Nucleosides. LX. Fluorocarbohydrates. XXII. Synthesis of 2-deoxy-2-fluoro-D-arabinose and 9-(2-deoxy-2-fluoro-α- and β-arabinofuranosyl)adenines . J. Org. Chem. , 34 : 2632 – 2636 .
  • Mikhailopulo , I. A. , Sivets , G. G. , Poopeiko , N. E. and Khripach , N. B. 1995 . Oxidation-reduction sequence for the synthesis of peracylated fluorodeoxy pentofuranosides . Carbohydr. Res. , 278 : 71 – 89 .
  • Mikhailopulo , I. A. , Pricota , T. I. , Sivets , G. G. and Altona , C. 2003 . 2′-Chloro-2′,3′-dideoxy-3′-fluoro-D-ribofuranosides: Synthesis, stereospecificity, some chemical transformations, and conformational analysis . J. Org. Chem. , 68 : 5897 – 5908 .
  • Gillard , J. W. and Israel , M. 1981 . Trimethylsilyl bromide as a mild, stereoselective anomeric brominating agent . Tetrahedron Lett. , 22 : 513 – 516 .
  • Jin , F. , Wang , D. , Confalone , P. N. , Pierce , M. E. , Wang , Z. , Xu , G. , Choudhury , A. and Nguyen , D. 2001 . (2R,3S,5S)-2-Acetoxy-3-fluoro-5-(p-toluoyloxymethyl)tetrahydrofuran: A key intermediate for the practical synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranofuranosyl)adenine (FddA) . Tetrahedron Lett. , 42 : 4787 – 4789 .
  • Martin , J. A. , Busnell , D. J. , Duncan , I. B. , Dunsdon , S. J. , Hall , M. J. , Machin , P. J. , Merret , J. H. , Parkes , K. E.B. , Roberts , N. A. , Thomas , G. J. , Galpin , S. A. and Kinchington , D. 1990 . Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1) . J. Med. Chem. , 33 : 2137 – 2145 .
  • 1H NMR (CD3OD; δTMS, ppm; J, Hz); compound 9–8.30 (d, 1H, J 8,2′F = 2.3; H-8); 8.21 (s, 1H; H-2); 6.53 (ddd, 1H, J 1′,2′ = 3.97; J 1′,2′F = 17.67; 4 J 1′,3′F = 1.86; H-1′); 5.50 (dddd, 1H, J 2′,3′ = 2.17; J 2′, 3′F = 12.82; gem J 2′,2′F = 50.52; H-2′); 5.46 (dddd, 1H, J 3′,4′ = 3.76; J 3′,2′F = 15.29; gem J 3′,3′F = 51.24; H-3′); 4.30 (dm, 1H, J 4′,5′ = 4.27; J 4′,5” = 4.85; J 4′,3′,F = 24.80; H-4′); 3.89 (ddd, 1H, gem J 5′,5” = 12.80; J 5′,3′ F(2′F) ≈ 1.0; H-5′); 3.85 (m, 1H; H-5”). Compound 10: 8.40 & 8.39 (2s, 2H; H-8 & H-2); 6.53 (dd, 1H, J 1′,2′ = 2.42; J 1′,2′F = 15.90; H-1′); 6.04 (ddt, 1H, J 2′,3′ = 2.74; J 2′, 3′F = 14.00; gem J 2′,2′F = 49.70; H-2′); 5.47 (dddd, 1H, J 3′,4′ = 3.90; J 3′,2′F = 15.90; gem J 3′,3′F = 51.70; H-3′); 4.81 (ddt 1H, J 4′,5′ = 5.04; J 4′,5” = 4.98; J 4′,3′,F = 21.16; H-4′); 3.83 (dd, 1H, gem J 5′,5” = 12.85; H-5′); 3.79 (ddd, 1H; J 5′,3′F = 1.15; H-5”)

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.