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Synlett 2004(2): 0335-0337  
DOI: 10.1055/s-2003-45000
LETTER
© Georg Thieme Verlag Stuttgart · New York

Efficient Preparation of 2-Deoxy-3,5-di-O-p-toluoyl-α-d-ribofuranosyl Chloride

Ilirian Dhimitruka, John SantaLucia Jr.*
Wayne State University, Department of Chemistry, 5101 Cass Ave., Detroit, MI 48202, USA
Fax: +1(313)5778822; e-Mail: jsl@chem.wayne.edu;
Further Information

Publication History

Received 25 August 2003
Publication Date:
18 December 2003 (online)

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Abstract

An efficient method for the synthesis of 1-O-methyl-3,5-di-O-p-toluoyl-2-deoxy-α/β-d-ribose is described. Upon treatment with HCl, 2-deoxy-3,5-di-O-p-toluoyl-α-d-ribofuranosyl chloride, previously unstable, was produced as a white solid, stable in air ­indefinitely.

Key words

1-O-methyl-3,5-di-O-p-toluoyl-2-deoxy-α/β-d-ribose - 2-deoxy-3,5-di-O-p-toluoyl-α-d-ribofuranosyl chloride - 1-O-methyl-2-deoxy-α/β-d-ribose - hydrogen chloride - p-toluic anhydride

    References

  • 1 Vorbruggen H. Ruh-Polenz C. Handbook of Nucleotide Synthesis  2001,  3 
    Google Scholar
  • 2 Bailly C. Waring MJ. Methods in Enzymology  2001,  340 (Drug-Nucleic Acid Interactions):  485 
    Google Scholar
  • 3 Montgomery J. Rideout JL. Henry DW. Nucleosides, Nucleotides and their Biological Application   Academic Press; New York: 1993.  p.19 
    Google Scholar
  • 4 Hoffer M. Chem. Ber.  1960,  93:  2777 
    CrossrefGoogle Scholar
  • 5 Hubbard AJ. Jones AS. Walker RT. Nucleic Acids Res.  1984,  12:  6827 
    Google Scholar
  • 6 Deriaz RE. Overend WG. Stacey M. Wiggins LF. J. Chem. Soc.  1949,  2836 
    Google Scholar
  • 7 Chin T.-M. Huang L.-K. Kan L. J. Chin. Chem. Soc.  1997,  44:  413 
    Google Scholar
  • 8 Zhang W. Ramasamy KS. Averett DR. Nucleosides Nucleotides  1999,  18:  12 
    Google Scholar
  • 10 Cherkasova EM. Bogatkov SV. Golovina ZP. Russ. Chem. Rev.  1977,  46:  246 
    Google Scholar
  • 11 Hubbard P. Brittain WJ. J. Org. Chem.  1998,  63:  677 
    CrossrefGoogle Scholar
9

Dhimitruka, I.; SantaLucia, J. Jr., manuscript in preparation.

12

p-Toluic anhydride was prepared as follows: p-Toluoyl chloride (1 equiv), water (0.5 equiv) and Et3N (1 equiv) were dissolved in acetone (0.03 mol/30 mL). The solution was stirred for 2 h then filtered. Et3N·HCl at 0 °C was washed with acetone (30 m L) and the combined acetone solutions evaporated to afford the product.