ArticleOrganic letters2010
One-pot etherification of purine nucleosides and pyrimidines.
Article in Organic letters, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 30 citations in OpenAlex.
- 1,2,3-Triazoles as leaving groups: SBeilstein journal of organic chemistry · 2021Article
- Improved Synthesis of Phosphoramidite-ProtectedMolecules (Basel, Switzerland) · 2020Article
- Catalytic Reductions Without External Hydrogen Gas: Broad Scope Hydrogenations with Tetrahydroxydiboron and a Tertiary Amine.Advanced synthesis & catalysis · 2020Article
- Facile Modifications at the C4 Position of Pyrimidine Nucleosides via In Situ Amide Activation with 1H-Benzotriazol-1-yloxy-tris(dimethyl-amino)phosphonium Hexafluorophosphate.Current protocols in nucleic acid chemistry · 2019Article
- Propargylated Purine Deoxynucleosides: New Tools for Fluorescence Imaging Strategies.Molecules (Basel, Switzerland) · 2019Article
- Facile functionalization at the C4 position of pyrimidine nucleosides via amide group activation with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and biological evaluations of the products.Organic & biomolecular chemistry · 2017Article
- Diarylmethanes through an Unprecedented Palladium-Catalyzed C-C Cross-Coupling of 1-(Aryl)methoxy-1ChemCatChem · 2015Article
- Cladribine Analogues via O⁶-(Benzotriazolyl) Derivatives of Guanine Nucleosides.Molecules (Basel, Switzerland) · 2015Article
- Facile synthesis of 1-alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents, mechanistic studies, and synthetic applications.Beilstein journal of organic chemistry · 2014Article
- Synthesis and biological properties of C-2 triazolylinosine derivatives.The Journal of organic chemistry · 2012Article
- Two-step, one-pot synthesis of inosine, guanosine, and 2'-deoxyguanosine O6-ethers via intermediate O6-(benzotriazol-1-yl) derivatives.Current protocols in nucleic acid chemistry · 2012Article
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2 authors at 1 institution in 1 country.
Funding
Abstract
A one-pot synthesis of ethers derived from inosine, guanosine, 2'-deoxyguanosine, and pyrimidinones is described. Exposure of the heterocycle to 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and Cs(2)CO(3) produces a reactive intermediate, which is converted to the desired ether by subsequent addition of an appropriate alcohol or phenol and Cs(2)CO(3). Although rapid formation of HMPA from BOP can occur in the presence of an alcohol and base, as demonstrated by the reaction with methanol, under appropriate conditions these heteroaryl ethers can be efficiently synthesized.
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