Abstract
The preparative method for the synthesis of 2-fluoroadenosine starting from commercially available guanosine was developed. It included the intermediate formation of 2-amino-6-azido-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine, which was isolated exclusively in the tetrazolo[5,1-i]-form {5-amino-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-7H -tetrazolo[5,1-i]purine}. The latter compound was converted by the Schiemann reaction to 6-azido-2-fluoro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine, which was isolated at an 80% yield after careful optimization of the process. The IR and 1H NMR spectroscopy data indicated the 6-azido-2-fluoropurine structure of the aglycone. The catalytic reduction of the azido group in 6-azido-2-fluoro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine to the amino moiety and the subsequent deacetylation by the routine procedure resulted in 2-fluoroadenosine at a total yield of 74%.
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Abbreviations
- 2F-Ado:
-
2-fluoroadenosine
- RT:
-
retention time
- Sug+ :
-
tri-O-acetyl-β-D-ribofuranosyl
- TBN:
-
tert-butyl nitrite
- TFA:
-
trifluoroacetic acid
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Original Russian Text © V.B. Berzin, E.V. Dorofeeva, V.N. Leonov, A.I. Miroshnikov, 2009, published in Bioorganicheskaya Khimiya, 2009, Vol. 35, No. 2, pp. 210–214.
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Berzin, V.B., Dorofeeva, E.V., Leonov, V.N. et al. The preparative method for 2-fluoroadenosine synthesis. Russ J Bioorg Chem 35, 193–196 (2009). https://doi.org/10.1134/S1068162009020071
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DOI: https://doi.org/10.1134/S1068162009020071