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Synlett 2004(14): 2585-2587  
DOI: 10.1055/s-2004-834809
LETTER
© Georg Thieme Verlag Stuttgart · New York

Study on Disulfur-Backboned Nucleic Acid: Part 1, Efficient Synthesis of 3′,5′-Dithio-2′-Deoxyadenosine

Hongchao Zheng, Changmei Cheng*, Hua Wang, Shanshan Xu, Yufen Zhao
Key Laboratory for Bioorganic Phosphorus Chemistry of Education Ministry, Department of Chemistry, School of Life Sciences and Engineering, Tsinghua University, 100084 Beijing, P. R. China
Fax: +86(10)62781695; e-Mail: chengcm@mail.tsinghua.edu.cn;
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Publication History

Received 17 July 2004
Publication Date:
20 October 2004 (online)

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Abstract

An efficient procedure is established to synthesize 3′,5′-dithio-2′-deoxyadenosine starting from 2′-deoxyadenosine in five steps in 33% overall yield. In this procedure, the key intermediate 9 was synthesized by twice SN2 reactions with twice 3′-configuration inversions and then it was deprotected to title compound by removing three acyl groups in one pot.

Key words

3′,5′-dithio-2′-deoxynucleoside - 3′,5′-dithio-2′-deoxyadenosine - disulfur-backboned nucleic acid - configuration inversions - synthesis

    References

  • 1a El-Barbary AA. Khodair AI. Pedersen EB. Nielsen C. Monatsh. Chem.  1994,  125:  1017 
    Google Scholar
  • 1b Reist EJ. Benitez A. Goodman L. J. Org. Chem.  1964,  29:  554 
    Google Scholar
  • 2a Eleuteri A. Reese CB. Song Q. J. Chem. Soc., Perkin Trans. 1  1996,  2237 
    CrossrefGoogle Scholar
  • 2b Chiba J. Tanaka K. Ohshiro Y. Miyake R. Hiraoka S. Shiro M. Shionoya M. J. Org. Chem.  2003,  68:  331 
    CrossrefGoogle Scholar
  • 3 Oae S. Okuyama T. Organic Sulfur Chemistry: Biochemical Aspects   CRC Press; Boca Raton, FL: 1992.  p.217-222  
    Google Scholar
  • 4 Nishino S. Yamamoto H. Nagato Y. Ishido Y. Nucleosides, Nucleotides Nucleic Acids  1986,  5:  159 
    Google Scholar
  • 5 Herdewijn PA. J. Org. Chem.  1988,  53:  5050 
    Google Scholar