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Issue 4, 2017
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The protecting-group free selective 3′-functionalization of nucleosides

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Abstract

The direct and chemoselective 3′-phosphoramidation, phosphorylation and acylation of nucleosides are described. Upon the discovery of a novel 3′-phosphorylamidation of therapeutic nucleoside analogues with DBU, we explored the mechanism of this rare selectivity through a combination of NMR spectroscopy and computational studies. The NMR and computational findings allowed us to develop a predictive computational model that accurately assesses the potential for 3′-functionalization for a broad range of nucleosides and nucleoside mimetics. The synthetic utility of this model was exemplified by demonstration on a broad scope of nucleosides and electrophiles yielding targets that were previously only accessible via a protection/deprotection sequence or an enzymatic approach.

Graphical abstract: The protecting-group free selective 3′-functionalization of nucleosides

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Publication details

The article was received on 18 Nov 2016, accepted on 06 Jan 2017, published on 18 Jan 2017 and first published online on 18 Jan 2017


Article type: Edge Article
DOI: 10.1039/C6SC05081F
Citation: Chem. Sci., 2017,8, 2804-2810
  • Open access: Creative Commons BY license
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    The protecting-group free selective 3′-functionalization of nucleosides

    J. M. McCabe Dunn, M. Reibarkh, E. C. Sherer, R. K. Orr, R. T. Ruck, B. Simmons and A. Bellomo, Chem. Sci., 2017, 8, 2804
    DOI: 10.1039/C6SC05081F

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