Synthesis of β-triphosphotriester pronucleotides

Authors

Yousef A. Beni, Tennessee State UniversityFollow
Chandravanu Dash, Meharry Medical CollegeFollow
Keykavous Parang, Chapman UniversityFollow

Document Type

Article

Publication Date

4-22-2015

Abstract

Dinucleoside phosphorochloridite were synthesized from phosphorus trichloride and three nucleoside analogues, 3-fluoro-2,3-dideoxythymidine (FLT), 2',3'-dideoxy-5-fluoro-3'- thiacytidine (FTC), and 2',3'-dideoxy-3'-thiacytidine (3TC), in a multistep synthesis. Polymerbound N-Boc p-acetoxybenzyl 5¢-O-2¢-deoxythymidine was reacted with dinucleoside phosphorochloridite in the presence of 2,6-lutidine, followed by the reaction with dodecyl alcohol and 5-(ethylthio)-1H-tetrazole, oxidation with tert-butyl hydroperoxide, and acidic cleavage, respectively, to afford the b-triphosphotriester derivatives containing three different nucleosides.

Comments

NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Letters. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version will subsequently be published in Tetrahedron Letters in 2015. DOI: 10.1016/j.tetlet.2015.03.036

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Recommended Citation

Beni, Y., Dash, C., Parang, K., Synthesis of β-triphosphotriester pronucleotides, Tetrahedron Letters (2015)
DOI: 10.1016/j.tetlet.2015.03.036

Copyright

Elsevier

Creative Commons License

This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.