Nucleosides, Nucleotides & Nucleic Acids 2003-10-01

Convenient synthesis of 2'-deoxy-2-fluoroadenosine from 2-fluoroadenine.

Song Ye, Martha M Rezende, Wei-Ping Deng, Kenneth L Kirk

Index: Nucleosides Nucleotides Nucleic Acids 22(10) , 1899-905, (2003)

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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 (alpha/beta = 1:1) in good yield. The alpha- and beta-anomers were separated by chromatography, and then desilylated to give compounds 1a and 1b.