Modified Nucleosides. II.¹ Economical Synthesis of 2′,3′-Dideoxycytidine

Sebastian M. Marcuccio CSIRO Division of Chemicals and Polymers Private Bag, 10, Clayton, Victoria, Australia, 3168

Bryan C. Elmes CSIRO Division of Chemicals and Polymers Private Bag, 10, Clayton, Victoria, Australia, 3168

George Holan CSIRO Division of Chemicals and Polymers Private Bag, 10, Clayton, Victoria, Australia, 3168

E. John Middleton CSIRO Division of Chemicals and Polymers Private Bag, 10, Clayton, Victoria, Australia, 3168

Abstract

An economical two pot synthesis of 2′,3′-dideoxycytidine (2) from N⁴-acetyl-cytidine (4) has been developed. The key feature of this sequence is the in situ reductive elimination of a mixture of 1-(3-bromo-3-deoxy-2,5-di-O-acetyl-β-D-xylofuranosyl)-N⁴-acetylcytosine (5) and 1-(2-bromo-3-deoxy-3,5-di-O-acetyl-β-D-arabinofuranosyl)-N⁴-acetylcytosine (6) and subsequent hydrogenation of the resultant olefin over palladised charcoal.

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Modified Nucleosides. II.¹ Economical Synthesis of 2′,3′-Dideoxycytidine

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Modified Nucleosides. II.1 Economical Synthesis of 2′,3′-Dideoxycytidine

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Modified Nucleosides. II.¹ Economical Synthesis of 2′,3′-Dideoxycytidine