121-39-1Relevant articles and documents
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Cristol,Norris
, (1954)
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Efficient and selective peracetic acid epoxidation catalyzed by a robust manganese catalyst
Garcia-Bosch, Isaac,Company, Anna,Fontrodona, Xavier,Ribas, Xavi,Costas, Miquel
, p. 2095 - 2098 (2008)
(Chemical Equation Presented) A manganese catalyst containing a tetradentate ligand derived from triazacyclononane exhibits high catalytic activity in epoxidation reactions using peracetic acid as oxidant. The system exhibits broad substrate scope and requires small (0.1-0.15 mol %) catalyst loading. The catalyst is remarkably selective toward aliphatic cis-olefins. Mechanistic studies point toward an electrophilic oxidant delivering the oxygen atom in a concerted step.
Dioxiranes: Synthesis and Reactions of Methyldioxiranes
Murray, Robert W.,Jeyaraman, Ramasubbu
, p. 2847 - 2853 (1985)
The peroxymonosulfate-acetone system produces dimethyldioxirane under conditions permitting distillation of the dioxirane from the synthesis vessel.The same conditions were used to prepare other methyldioxiranes.Solutions of dimethyldioxirane prepared in this manner were used to study its chemical and spectroscopic properties.The caroate-acetone system was also used to study the chemistry of in situ generated dimethyldioxirane.
Metal-free ring-opening of epoxides with potassium trifluoroborates
Roscales, Silvia,Csaky, Aurelio G.
, p. 454 - 456 (2014)
The ring-opening of epoxides with potassium trifluoroborates proceeds smoothly in the presence of trifluoroacetic anhydride under metal-free conditions. The reactions are regioselective and afford a single diastereomer. Both electron-rich and electron-poor aryltrifluoroborates are tolerated.
Hypervalent Iodine(III)-Catalyzed Epoxidation of β-Cyanostyrenes
Mangaonkar, Saeesh R.,Singh, Fateh V.
, p. 4473 - 4486 (2019/11/21)
A convenient approach for the synthesis of β-cyanoepoxides is illustrated by iodine(III)-catalyzed epoxidation of electron-deficient β-cyanostyrenes, wherein the active catalytic iodine(III) species was generated in situ. The epoxidation of β-cyanostyrenes was performed using 10 molpercent PhI as precatalyst in the presence of 2.0 equivalents Oxone as an oxidant and 2.4 equivalents of TFA as an additive at room temperature under ultrasonic radiations. The β-cyanoepoxides were isolated in good to excellent yields in a short reaction time.
CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE
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Paragraph 000578; 000579; 000960; 000961, (2018/01/17)
Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.
Enantioselective bio-hydrolysis of various racemic and meso aromatic epoxides using the recombinant epoxide hydrolase Kau2
Zhao, Wei,Kotik, Michael,Iacazio, Gilles,Archelas, Alain
, p. 1895 - 1908 (2015/06/02)
Abstract Epoxide hydrolase Kau2 overexpressed in Escherichia coli RE3 has been tested with ten different racemic and meso α,β-disubstituted aromatic epoxides. Some of the tested substrates were bi-functional, and most of them are very useful building blocks in synthetic chemistry applications. As a general trend Kau2 proved to be an extremely enantioselective biocatalyst, the diol products and remaining epoxides of the bioconversions being obtained - with two exceptions - in nearly enantiomerically pure form. Furthermore, the reaction times were usually very short (around 1 h, except when stilbene oxides were used), and the use of organic co-solvents was well tolerated, enabling very high substrate concentrations (up to 75 g/L) to be reached. Even extremely sterically demanding epoxides such as cis- and trans-stilbene oxides were transformed on a reasonable time scale. All reactions were successfully conducted on a 1 g preparative scale, generating diol- and epoxide-based chiral synthons with very high enantiomeric excesses and isolated yields close to the theoretical maximum. Thus we have here demonstrated the usefulness and versatility of lyophilized Escherichia coli cells expressing Kau2 epoxide hydrolase as a highly enantioselective biocatalyst for accessing very valuable optically pure aromatic epoxides and diols through kinetic resolution of racemates or desymmetrization of meso epoxides.
