A convenient synthesis of 2'-deoxy-2-fluoroadenosine; a potential prodrug for suicide gene therapy

Article abstract of DOI:10.1080/15257770008035007

A convenient synthesis of 2'-deoxy-2-fluoro-adenosine (1) is described. Deaminative fluorination of 2-aminoadenosine (2) followed by silylation of the 3', 5'-hydroxyl groups gave the corresponding 2-fluoroadenosine derivative 4 in good yield. Thiocarbonylation of 4 to thiocarbonylimidazolyl derivative 5a followed by treatment with an excess of tris(trimethylsilyl)silane (TTMSS) and tert-butyl peroxide in toluene at 80 °C was found to affect an efficient deoxygenation to the corresponding 2'- deoxy derivative 6. Desilylation of 6 by Et₄NF in CH₃CN afforded 1 in high yield.

Full text of DOI:10.1080/15257770008035007

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A Convenient Synthesis of 2′-Deoxy-2-
fluoroadenosine; a Potential Prodrug for
Suicide Gene Therapy
Abdalla E. A. Hassan a , Anita T. Shortnacy-fowler a , John A.
Montgomery a & John A. Secrist III a
a Drug Discovery Division, Southern Research Institute , P.O. Box
55305, Birmingham, AL, 35255-5305, U. S. A.
Published online: 24 Sep 2006.
To cite this article: Abdalla E. A. Hassan , Anita T. Shortnacy-fowler , John A. Montgomery &
John A. Secrist III (2000) A Convenient Synthesis of 2′-Deoxy-2-fluoroadenosine; a Potential
Prodrug for Suicide Gene Therapy, Nucleosides, Nucleotides and Nucleic Acids, 19:3, 559-565, DOI:
10.1080/15257770008035007
To link to this article: http://dx.doi.org/10.1080/15257770008035007
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