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Synthesis 1990; 1990(10): 900-905
DOI: 10.1055/s-1990-27048
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Synthesis of 3′-Fluoro-3′-deoxyadenosine Starting from Adenosine

Carlo Battistini* , Antonio Giordani, Antonella Ermoli, Giovanni Franceschi
  • *Farmitalia Carlo Erba (Erbamont Group) - Research and Development, via dei Gracchi 35, I-20146 Milano, Italy
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Publication Date:
17 September 2002 (online)

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A new synthesis of 3′-fluoro-3′-deoxyadenosine is described. Start- ing from adenosine via a suitably protected intermediate by triflate activation and nucleophilic displacement with sodium acetate, the "xylo" epimer is obtained in two cases with different silyl groups protecting the 2′-position. Treatment of the xylo derivatives with diethylaminosulphur trifluoride gives the corresponding 3′-fluoro derivatives with inversion of the configuration. The reaction se- quence affords protected derivatives allowing selective deblocking of the 5′ or 2′-position.