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Original Articles

SYNTHESIS OF 2′,3′-DIDEOXY-2′,3′-DIDEHYDRO NUCLEOSIDES VIA A SERENDIPITOUS ROUTE

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Pages 1263-1266 | Published online: 07 Feb 2007

REFERENCES

  • Sanghvi , Y. S. , Andrade , M. , Deshmukh , R. R. , Holmberg , L. , Scozzari , A. N. and Cole , D. L. 1999 . Manual of Antisense Methodology Edited by: Hartmann , G. and Endres , S. 3 – 23 . Kluwer Academic Publishers .
  • Sanghvi , Y. S. 1999 . “ DNA with Altered Backbones in Antisense Applications ” . In Comprehensive Natrual Products Chemistry, DNA and Aspects of Molecular Biology Edited by: Barton , D. H.R Editors-in-Chief , Nakanishi , K. and Kool , E. T. Vol. 7 , 258 – 311 . Pergamon Press .
  • The bulk price for 2′-deoxynucleosides isolated from fish milt is around $1, 000/Kg
  • Freskos , J. N. and Senaratne , P. A. US Patent 4, 914, 233 . April 3, 1990 .
  • Shiragami , H. , Amino , Y. , Honda , Y. , Arai , M. , Tanaka , Y. , Iwagami , H. , Yukawa , T. and Izawa , K. 1996 . Nucleosides Nucleotides , 15 : 31 – 45 .
  • Cell assembly for electrolysis: The cell was home built using a glass beaker fitted with a compartment (fritted disk at the bottom) containing a platinum plate (2 × 2 cm, 0.1 mm thick) as anode and mercury cathode (pool at the bottom). The top was covered with a plate with an inlet and outlet for argon, a thermometer and an Ag/Ag+ (1 mm silver wire immersed in 0.1 M AgNO3 in acetonitrile) reference electrode. Cyclic and linear sweep voltammatries were conducted on the electrolysis solutions prior to the electrolysis to determine the optimum reduction potentials. Electrochemical reductions were performed in methanol or acetonitrile with tetraethylammonium p-toluenesulfonate (0.2 M) as electrolyte. The concentration of the electrolyte was maintained in a 5-fold excess relative to the electroactive species. The nucleosidic substrate (5 mmol) was added and the stirred solution was electrolysed under argon at an initial constant potential of −1.9 V for 1 h. The progress of the reaction was followed by TLC and most of the starting material was consumed within 1 h. Upon completion of the reaction, the solution was concentrated under vacuum and the residue purified by short silica gel column chromatography. The yield of the isolated product was always >80%. The deprotected (NH4OH) products were identical (TLC, UV, NMR) with an authentic sample
  • Adachi , T. , Iwaski , T. , Inoue , I. and Miyoshi , M. 1979 . J. Org. Chem. , 44 : 1404 – 1409 .
  • Johansen , O. , Marcuccio , S. M. and Mau , A. W.-H. 1994 . Aust. J. Chem. , 47 : 1843 – 1850 .

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