Preparation of Potential Cell-Permeant Nucleoside-2′, 3′-Cyclic Phosphate Precursors

S Battaggia, EE Smith, JS Vyle

Index: Battaggia, Simone; Smith, Emma E.; Vyle, Joseph S. Nucleosides, Nucleotides and Nucleic Acids, 2007 , vol. 26, # 3 p. 245 - 254

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Abstract

Uridine-3′-phosphorothiolate triesters bearing lipophilic moieties were prepared via Michaelis-Arbuzov chemistry. Subsequent deprotection of the S-cholesteryl phosphorothiolate triester afforded the corresponding diester which underwent spontaneous Cyclization to cleanly afford uridine 2′, 3′-cyclic phosphate. This transesterification reaction could be expedited by treatment with iodine under mild, neutral conditions.