Acyclic analogs of nucleosides. Synthesis of 1,5-dihydroxy-3-oxa-2-pentyl derivatives of nucleic bases
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A convenient method for the synthesis of 1,5-dihydroxy-3-oxa-2-pentyl derivatives of nucleic bases, which consists in the condensation of trimethylsilyl derivatives of nucleic bases with 1,2,5-triacetoxy-3-oxapentane in the presence of SnCl4, is proposed. Optically active derivatives — (R)- and (S)-1-(1,5-dihydroxy-3-oxa-2-pentyl)uracil, respectively — were obtained by periodate oxidation of α-L- and α-D-arabinopyranosyluracil.
KeywordsOxidation Organic Chemistry Nucleoside Uracil Trimethylsilyl
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