Synthesis of 3′-Fluoro-3′-deoxy-N⁶-cyclopentyladenosine

G. Ceulemans Rega Institute for Medical Research, Laboratory of Medicinal Chemistry, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium

R. Busson Rega Institute for Medical Research, Laboratory of Medicinal Chemistry, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium

N. Weyns Rega Institute for Medical Research, Laboratory of Medicinal Chemistry, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium

F. Vandendriessche Rega Institute for Medical Research, Laboratory of Medicinal Chemistry, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium

J. Rozenski Rega Institute for Medical Research, Laboratory of Medicinal Chemistry, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium

A. IJzerman Center for Bio-pharmaceutical Sciences, Division of Medicinal Chemistry, Leiden University, 2300 RA, Leiden, The Netherlands

P. Herdewijn Rega Institute for Medical Research, Laboratory of Medicinal Chemistry, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium

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Abstract

Starting from 9-(β-D-xylofuranosyl)-6-chloropurine, the title compound was prepared in four steps. Reaction with cyclopentylamine followed by treatment of the 2′-O,5′-O-ditritylated material with diethylaminosulfur trifluoride (DAST), yielded after deprotection the desired compound.

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Synthesis of 3′-Fluoro-3′-deoxy-N⁶-cyclopentyladenosine

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Synthesis of 3′-Fluoro-3′-deoxy-N6-cyclopentyladenosine

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Synthesis of 3′-Fluoro-3′-deoxy-N⁶-cyclopentyladenosine