Synthesis of Novel 2,2'-Anhydro-<i>L</i>-threosylpyrimidine Phosphonates

Zhu, Chuantao; Wang, Song; Zhao, Yifan; Herdewijn, Piet; Liu, Fengwu

doi:10.6023/cjoc202303015

Cited by 1 publication

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References 17 publications

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“…Zhu reported that the synthesis of 2,2′-O-cyclouridine analogues could be easily performed using diethylaminosulfur trifluoride (DAST) as cyclisation agent [19]. In the representative example (Scheme 3), pyrimidine L-threonucleoside phosphonate ester 9 was treated with DAST in dichloromethane at -20 °C which resulted in corresponding 2,2′-O-cyclo-L-threonucleoside phosphonate ester 10.…”

Section: The Synthesis Of Pyrimidine Cyclonucleosidesmentioning

confidence: 99%

Synthesis and applications of cyclonucleosides: an update (2010–2023)

Burchiellaro,

Mieczkowski

2023

Mol Divers

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Cyclonucleosides are a group of nucleoside derivatives which, in addition to the classical N-glycosidic bond, have an additional covalent bond (linker, bridge) in their structure, which connects the heterocyclic base and sugar ring. The majority of them have been discovered in the laboratory; however, few such compounds have also been found in natural sources, including metabolites of sponges or radical damage occurring in nucleic acids. Due to their structural properties—rigid, fixed conformation—they have found wide applications in medicinal chemistry and biochemistry as biocides as well as enzyme inhibitors and molecular probes. They have also found use as convenient synthetic tools for the preparation of new nucleoside analogues, enabling structural modifications of both the sugar ring and heterocyclic base. This review summarizes the recent progress in the synthesis of various purine and pyrimidine cyclonucleosides using diverse chemical approaches based on radical, “click”, metal-mediated, and other types of reactions. It also presents recent reports concerning possible applications in medicinal chemistry, as well as their applications as valuable key intermediates in the synthesis of sugar- and base-modified nucleoside analogues and heterocyclic compounds. Graphical abstract

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Section: The Synthesis Of Pyrimidine Cyclonucleosidesmentioning

confidence: 99%