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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 12
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Original Articles

Stereoselective Preparation of 1-[5-O-(tert-Butyldimethylsilyl)-2,3-dideoxy-3-iodo-β-D-threo-pentofuranosyl]thymine from Thymidine: An Efficient Entry to 3′,4′-Unsaturated Nucleoside

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Pages 1758-1764 | Received 12 Apr 2009, Published online: 17 May 2010

REFERENCES

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  • For a review regarding the synthesis and antiviral activity of 4′-substituted nucleosides, see Hayakawa , H. ; Kohgo , S. ; Kitano , K. ; Ashida , N. ; Kodama , E. ; Mitsuya , H. ; Ohrui , H. Potential for 4′-C-substituted nucleosides for the treatment of HIV-1 . Antiviral Chem. Chemother. 2004 , 15 , 169 – 187 .
  • (a) Haraguchi , K. ; Tanaka , H. ; Itoh , Y. ; Yamaguchi , K. ; Miyasaka , T. Allylic substitution of 3′,4′-unsaturated nucleosides: Organosilicon-based stereoselective access to 4′-C-branched 2′,3′-didehydro-2′,3′-dideoxyribonucleosides . J. Org. Chem. 1996 , 61 , 851 – 858 ; (b) Haraguchi , K. ; Itoh , Y. ; Takeda , S. ; Honma , Y. ; Tanaka , H. ; Nitanda , T. ; Baba , Y. ; Dutschman , G. ; Cheng , Y.-C. Synthesis and anti-HIV activity of 4′-C-cyaco-2′,3′-didehydro-3′-deoxythymdine . Nucleosides, Nucleotides Nucl. Acids 2004 , 23 , 647 – 654 .
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  • For physical data of 7 and 14, see Takahashi , Y. ; Honda , Y. ; Tsuchiya , T. Synthesis of (3′R)-3′-deoxy-3′-C-nitromethylthymidine . Carbohydr. Res. 1995 , 270 , 77 – 83 .
  • For physical data of 17, see Adbel-Megied , A. E.-S. ; Hansen , P. ; Pedersen , E. B. ; Nielsen , C. M. New synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides . Acta Chem. Scand. 1991 , 45 , 1060 – 1063 . For physical data of 18, see Sanghvi , Y. S. ; Bharadwaj , R. ; Debart , F. ; Mesmaeker , A. D. Efficient and stereoselective synthesis of 3′-deoxy 3′-C-branched-chain substituted thymidine . Synthesis 1994 , 1163 – 1166 .
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