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

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

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Received: 11 September 2013; in revised form: 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)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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)
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MDPI and ACS Style

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.

AMA Style

Peterson TV, Streamland TUB, Awad AM. A Tractable and Efficient One-Pot Synthesis of 5'-Azido-5'-deoxyribonucleosides. Molecules. 2014; 19(2):2434-2444.

Chicago/Turabian Style

Peterson, Theodore V.; Streamland, Tobin U.B.; Awad, Ahmed M. 2014. "A Tractable and Efficient One-Pot Synthesis of 5'-Azido-5'-deoxyribonucleosides." Molecules 19, no. 2: 2434-2444.

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