4162-61-2Relevant articles and documents
Synthesis and anti-HIV evaluation of new acyclic phosphonate nucleotide analogues and their bis(SATE) derivatives
Li, Hua,Hong, Joon Hee
, p. 581 - 590 (2010)
This article describes a very simple route for synthesizing novel lipophilic phosphonate bis(t-bu-SATE) prodrugs of acyclic cyclopentenylated nucleosides such as adenine 17 and cytosine 18. The key intermediate 6 was constructed via a ring-closing metathesis of compound 5, which could be readily prepared from diethylmalonate 4. The chemical stability of the bis(SATE) derivatives was tested at neutral (pH = 7.2) and slightly acid (milli-Q water, pH = 5.5) pH. The synthesized compounds were evaluated as potential antiviral agents against HIV-1 virus.
Ruthenium Removal Using Silica-Supported Aromatic Isocyanides
Gregg, Zackary R.,Glickert, Elise,Xu, Ruoshui,Diver, Steven T.
supporting information, (2021/05/13)
New silica gel scavengers containing aromatic isocyanides have been synthesized and evaluated for Ru removal. A thiol-ene click reaction was used to attach the isocyanide precursor to a thiol-containing siloxane. Conventional methods for grafting to silica gel at elevated temperature resulted in significant hydrolysis of the isocyanide. A novel cleavage reaction was developed to quantitate the amount of surface-loaded isocyanide. Binding by the new materials was comparatively evaluated for a variety or Ru carbene catalysts. The optimal conditions were extended to two ring-closing metatheses (RCM). The residual Ru was determined by inductively coupled plasma mass spectrometry (ICP-MS). For facile RCM reactions, the UV data agreed with the ICP-MS results. However, more difficult RCM did not correlate well with the UV data. This was interpreted in terms of varying extent of catalyst decomposition. In all cases, isocyanide scavenger reagents were found to be superior to commonly used, silica gel-based metal scavengers.
Kinetic benchmarking reveals the competence of prenyl groups in ring-closing metathesis
Bahou, Karim A.,Braddock, D. Christopher,Meye, Adam G.,Savage, G. Paul
supporting information, p. 5332 - 5335 (2017/11/07)
A series of prenyl-containing malonates are kinetically benchmarked against the standard allyl-containing congeners using a ruthenium benzylidene precatalyst for ringclosing metatheses. The prenyl grouping is found to be a superior acceptor olefin compared to an allyl group in RCM processes with ruthenium alkylidenes derived from terminal alkenes. The prenyl group is also found to be a highly competent acceptor for a ruthenium alkylidene derived from a 1, 1-disubstituted olefin in a RCM process.
Simple, chemoselective hydrogenation with thermodynamic stereocontrol
Iwasaki, Kotaro,Wan, Kanny K.,Oppedisano, Alberto,Crossley, Steven W. M.,Shenvi, Ryan A.
supporting information, p. 1300 - 1303 (2014/02/14)
Few methods permit the hydrogenation of alkenes to a thermodynamically favored configuration when steric effects dictate the alternative trajectory of hydrogen delivery. Dissolving metal reduction achieves this control, but with extremely low functional group tolerance. Here we demonstrate a catalytic hydrogenation of alkenes that affords the thermodynamic alkane products with remarkably broad functional group compatibility and rapid reaction rates at standard temperature and pressure.