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4. Preparation of Potential Cell-Permeant Nucleoside-2',3'-Cyclic Phosphate Precursors.

Author

Battaggia, Simone, Smith, EmmaE., and Vyle, JosephS.

Subjects
*URIDINE, *AZARIBINE, *PHOSPHATES, *IODINE, *MOIETIES (Chemistry)
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. [ABSTRACT FROM AUTHOR]

Published
2007
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