23709-41-3Relevant articles and documents
Asymmetric Synthesis of 2′- C-Methyl-4′-selenonucleosides as Anti-Hepatitis C Virus Agents
Lee, Hyejin,Jarhad, Dnyandev B.,Yu, Jinha,Lee, Choongho,Jeong, Lak Shin
, p. 14414 - 14426 (2019)
In search of a new template for anti-hepatitis C virus (HCV) agents, we designed and synthesized the 2′-C-methyl-4′-selenopyrimidine and -purine nucleosides and their phosphoramidate prodrugs to replace a furanose oxygen of anti-HCV nucleos(t)ides with a selenium atom on the basis that selenium is a chemical isostere of oxygen. These nucleosides are expected to show different physicochemical properties such as better lipophilicity which might enhance the penetration across cell membranes and the conformational constraint induced by a bulky selenium atom in the sugar ring. The 2′-C-methyl-4′-selenopyrimidine and -purine nucleosides 8 and 9 were synthesized from 2-C-methyl-d-ribono-γ-lactone (14) via construction of 2-C-methyl-d-selenosugar 18 through C-4 epimerization and SN2 cyclization with Se2- as key steps. The key 4′-selenosugar was converted to the 2′-C-methyl-4′-selenopyrimidine and -purine nucleosides using Pummerer-type rearrangement and Vorbrüggen glycosylation, respectively. In addition, the ProTide strategy has been applied to synthesize the adenine and uracil phosphoramidate derivatives 10a and 10b to overcome the limitations associated with parent nucleosides such as inefficient conversion to their corresponding 5′-monophosphate form and poor cellular uptake. The regio- and stereochemistry of 4′-selenonucleosides were confirmed by 2D NOESY NMR spectroscopy and X-ray crystallography. None of the final pyrimidine and purine nucleosides and their prodrugs exhibited significant anti-HCV activity up to 100 μM.
Homochiral carbon branched piperidines from carbon branched sugar lactones: 4-C-methyl-deoxyfuconojirimycin (DFJ) and its enantiomer-removal of glycosidase inhibition
Hotchkiss, David J.,Kato, Atsushi,Odell, Barbara,Claridge, Timothy D.W.,Fleet, George W.J.
, p. 500 - 512 (2007)
The value of readily available 2-C-methyl aldonic acids in short syntheses of carbon branched piperidines containing quaternary centers is demonstrated. The effect of the introduction of a 4-C-methyl group into piperidine imino sugar inhibitors of l-fucosidases and d-galactosidases is reported.
PHOTOACID GENERATOR, PHOTORESIST COMPRISING THE PHOTOACID GENERATOR, AND COATED ARTICLE COMPRISING SAME
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Paragraph 0091-0093, (2016/12/16)
A photoacid generator has the formula (I): wherein R1, R2, R3, L1, L2, L3 X, Z+, a, b, c, d, p, q, and r, are defined herein. A photoresist comprises the photoacid generator, and a coated article comprises the photoresist. The photoresist can be used to form an electronic device.
SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF
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Paragraph 1135; 1136, (2016/03/08)
Disclosed herein are nucleosides, nucleotides and nucleotide analogs, methods of synthesizing the same and methods of treating diseases and/or conditions such as a Coronaviridae virus, a Togaviridae virus, a Hepeviridae virus and/or a Bunyaviridae virus infection with one or more nucleosides, nucleotides and nucleotide analogs.