Download PDF
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;
Further Information

Publication History

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

    Permissions and Reprints All articles of this category

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