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

Authors
Hassan, AEA Shortnacy-Fowler, AT Montgomery, JA Secrist, JA
Citation
Aea. Hassan et al., A convenient synthesis of 2 '-deoxy-2-fluoroadenosine; a potential prodrugfor suicide gene therapy, NUCLEOS NUC, 19(3), 2000, pp. 559-565
Citations number
19
Categorie Soggetti
Biochemistry & Biophysics
Journal title
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
ISSN journal
15257770 → ACNP
Volume
19
Issue
3
Year of publication
2000
Pages
559 - 565
Database
ISI
SICI code
1525-7770(2000)19:3<559:ACSO2'>2.0.ZU;2-B
Abstract
A convenient synthesis of 2'-deoxy-2-fluoro-adenosine (1) is described. Dea minative 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 derivati ve 5a followed by treatment with an excess of tris(trimethylsilyl)silane (T TMSS) and tert-butyl peroxide in toluene at 80 degrees C was found to affec t an efficient deoxygenation to the corresponding 2'-deoxy derivative 6. De silylation of 6 by Et4NF in CH3CN afforded 1 in high yield.