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Molecules 2014, 19(2), 2434-2444; doi:10.3390/molecules19022434
Article

A Tractable and Efficient One-Pot Synthesis of 5'-Azido-5'-deoxyribonucleosides

,
 and
*
Chemistry Program, California State University Channel Islands, One University Drive, Camarillo, CA 93012, USA
* Author to whom correspondence should be addressed.
Received: 11 September 2013 / Revised: 11 February 2014 / Accepted: 12 February 2014 / Published: 21 February 2014
(This article belongs to the Special Issue Synthesis of Nucleosides, Nucleotides and Their Derivatives)
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Abstract

Synthetic routes to 5'-azidoribonucleosides are reported for adenosine, cytidine, guanosine, and uridine, resulting in a widely applicable one-pot methodology for the synthesis of these and related compounds. The target compounds are appropriate as precursors in a variety of purposive syntheses, as the synthetic and therapeutic relevance of azido- and amino-modified nucleosides is expansive. Furthermore, in the conversion of alcohols to azides, these methods offer a tractable alternative to the Mitsunobu and other more difficult reactions.
Keywords: modified nucleosides; 5'-azido nucleosides; Appel reaction; Mitsunobu reaction; antisense oligonucleotides; ribonucleic guanidine (RNG) modified nucleosides; 5'-azido nucleosides; Appel reaction; Mitsunobu reaction; antisense oligonucleotides; ribonucleic guanidine (RNG)
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Peterson, T.V.; Streamland, T.U.B.; Awad, A.M. A Tractable and Efficient One-Pot Synthesis of 5'-Azido-5'-deoxyribonucleosides. Molecules 2014, 19, 2434-2444.

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