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Nucleosides, Nucleotides & Nucleic Acids Volume 22, 2003 - Issue 10
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Original Articles

Convenient Synthesis of 2′-Deoxy-2-fluoroadenosine from 2-Fluoroadenine

Song Ye Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland, USA
,
Martha M. Rezende Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland, USA
,
Wei-Ping Deng Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland, USA
&
Kenneth L. Kirk Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland, USA; Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, MD, 20892, USACorrespondence[email protected]
Pages 1899-1905 | Received 28 Feb 2003, Accepted 09 Jun 2003, Published online: 31 Aug 2006
 
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Abstract

A convenient synthesis of 2′-deoxy-2-fluoroadenosine from commercially available 2-fluoroadenine is described. The coupling reaction of silylated 2-fluoroadenine with phenyl 3,5-bis[O-(t-butyldimethylsilyl)]-2-deoxy-1-thio-D-erythro-pentofuranoside gave the corresponding 2-fluoro-2′-deoxyadenosine derivative (α/β =1:1) in good yield. The α- and β-anomers were separated by chromatography, and then desilylated to give compounds 1a and 1b.

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