148903-86-0Relevant articles and documents
Highly Stereoselective Glycosylation Reactions of Furanoside Derivatives via Rhenium (V) Catalysis
Casali, Emanuele,Othman, Sirwan T.,Dezaye, Ahmed A.,Chiodi, Debora,Porta, Alessio,Zanoni, Giuseppe
, p. 7672 - 7686 (2021/06/21)
A novel approach for the formation of anomeric carbon-functionalized furanoside systems was accomplished through the employment of an oxo-rhenium catalyst. The transformation boasts a broad range of nucleophiles including allylsilanes, enol ethers, and aromatics in addition to sulfur, nitrogen, and hydride donors, able to react with an oxocarbenium ion intermediate derived from furanosidic structures. The excellent stereoselectivities observed followed the Woerpel model, ultimately providing 1,3-cis-1,4-trans systems. In the case of electron-rich aromatic nucleophiles, an equilibration occurs at the anomeric center with the selective formation of 1,3-trans-1,4-cis systems. This anomalous result was rationalized through density functional theory calculations. Different oxocarbenium ions such as those derived from dihydroisobenzofuran, pyrrolidine, and oxazolidine heterocycles can also be used as a substrate for the oxo-Re-mediated allylation reaction.
Synthesis and Characterization of Oligonucleotides Containing the C4′-Oxidized Abasic Site Produced by Bleomycin and Other DNA Damaging Agents
Kim, Jaeseung,Gil, Jun Mo,Greenberg, Marc M.
, p. 5882 - 5885 (2007/10/03)
Selective introduction of damage: The C4′-position of DNA serves as the site of attack for a number of DNA damaging agents, including bleomycin. The C4′-abasic site is a major product found in damaged DNA following abstraction of the hydrogen atom from th
