Synthesis of 1-[2-(Hydroxymethyl)cyclohexyl]pyrimidine Analogues of Nucleosides: A Comparative Study

Abstract

The synthesis of a new series of 1,2-disubstituted carbonucleosides analogues of pyrimidine (cyclohexane derivatives) is reported. For the synthesis of the uridine analogue 5a, either construction of the base on the amino group of the amino alcohol 3 or on the amido group of the predecessor β-lactam 1 was more efficient than condensation of the base with a protected diol. The cis-configuration of 5a was confirmed by X-ray crystallography. Compound 5a was halogenated with Cl, Br and I at uracil position 5.

Key words

amino alcohols - cyclizations - heterocycles - Mitsunobu reaction - nucleosides

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Complete crystallographic data have been deposited at the Cambridge Crystallogrphic Data Centre under the number CCDC-235125. Copies can be obtained free of charge from CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: [phone]; e-mail: [e-mail]].