4.8 Article

Access to 3-Deazaguanosine Building Blocks for RNA Solid-Phase Synthesis Involving Hartwig-Buchwald C-N Cross-Coupling

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ORGANIC LETTERS
卷 21, 期 11, 页码 3900-3903

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00855

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资金

  1. Austrian Science Fund FWF [I1040, P27947, P31691, P28725, P30370]
  2. Austrian Research Promotion Agency FFG [West Austrian] [BioNMR 858017]
  3. Austrian Science Fund (FWF) [P31691, P30370, P27947] Funding Source: Austrian Science Fund (FWF)

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3-Deazaguanosine (c(3)G) and phosphoramidite derivatives thereof that allow incorporation of this modification into RNA are needed for atomic mutagenesis experiments to explore mechanistic aspects of ribozyme catalysis. Here, we report a practical synthesis for c(3)G phosphoramidites from inexpensive starting materials. The key reaction sequence is a silyl-Hilbert-Johnson nucleosidation followed by Hartwig-Buchwald cross-coupling to achieve the N-2-phenoxyacetyl protected c(3)G nucleoside.

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