Sharpless Epoxidation
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Sharpless Epoxidation
The Sharpless epoxidation reaction is an enantioselective chemical reaction to prepare 2,3-epoxyalcohols from primary and secondary allylic alcohols. The oxidizing agent is ''tert''-butyl hydroperoxide. The method relies on a catalyst formed from titanium tetra(isopropoxide) and diethyl tartrate. 2,3-Epoxyalcohols can be converted into diols, aminoalcohols, and ethers. The reactants for the Sharpless epoxidation are commercially available and relatively inexpensive. K. Barry Sharpless was awarded the 2001 Nobel Prize in Chemistry for this and related work on asymmetric oxidations. The prize was shared with William S. Knowles and Ryōji Noyori. Catalyst 5–10 mol% of the catalyst is typical. The presence of 3Å molecular sieves (3Å MS) is necessary. The structure of the catalyst is uncertain although it is thought to be a dimer of []. Selectivity The epoxidation of allylic alcohols is a well-utilized conversion in fine chemical synthesis. The chirality of the produ ...
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Karl Barry Sharpless
Karl Barry Sharpless (born April 28, 1941) is an American chemist and a two-time Nobel laureate in Chemistry known for his work on stereoselective reactions and click chemistry. Sharpless was awarded half of the 2001 Nobel Prize in Chemistry "for his work on chirally catalysed oxidation reactions", and one third of the 2022 prize, jointly with Carolyn R. Bertozzi and Morten P. Meldal, "for the development of click chemistry and bioorthogonal chemistry". Sharpless is the fifth person (in addition to two organizations), to have twice been awarded a Nobel prize, along with Marie Curie, John Bardeen, Linus Pauling and Frederick Sanger, and the third to have been awarded two prizes in the same discipline (after Bardeen and Sanger). Early life and education Sharpless was born April 28, 1941, in Philadelphia, Pennsylvania. His childhood was filled with summers at his family cottage on the Manasquan River in New Jersey. This is where Sharpless developed a love for fishing that he wo ...
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Mnemonic
A mnemonic ( ) device, or memory device, is any learning technique that aids information retention or retrieval (remembering) in the human memory for better understanding. Mnemonics make use of elaborative encoding, retrieval cues, and imagery as specific tools to encode information in a way that allows for efficient storage and retrieval. Mnemonics aid original information in becoming associated with something more accessible or meaningful—which, in turn, provides better retention of the information. Commonly encountered mnemonics are often used for lists and in auditory form, such as short poems, acronyms, initialisms, or memorable phrases, but mnemonics can also be used for other types of information and in visual or kinesthetic forms. Their use is based on the observation that the human mind more easily remembers spatial, personal, surprising, physical, sexual, humorous, or otherwise "relatable" information, rather than more abstract or impersonal forms of informa ...
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Terpenes
Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n > 1. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes are further classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), as examples. The terpene alpha-pinene, is a major component of the common solvent, turpentine. History and terminology The term ''terpene'' was coined in 1866 by the German chemist August Kekulé to denote all hydrocarbons having the empirical formula C10H16, of which camphene was one. Previously, many hydrocarbons having the empirical formula C10H16 had been called "camphene", but many other hydrocarbons of the same composition had had different names. Kekulé coined the term "terpene" in order to reduce the confusion. The name "terpene" is a shortened form of "terpentine", an obsolete spelling of "turpentine". Although sometimes u ...
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Saccharides
In organic chemistry, a carbohydrate () is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1 (as in water) and thus with the empirical formula (where ''m'' may or may not be different from ''n''), which does not mean the H has covalent bonds with O (for example with , H has a covalent bond with C but not with O). However, not all carbohydrates conform to this precise stoichiometric definition (e.g., uronic acids, deoxy-sugars such as fucose), nor are all chemicals that do conform to this definition automatically classified as carbohydrates (e.g. formaldehyde and acetic acid). The term is most common in biochemistry, where it is a synonym of saccharide (), a group that includes sugars, starch, and cellulose. The saccharides are divided into four chemical groups: monosaccharides, disaccharides, oligosaccharides, and polysaccharides. Monosaccharides and disaccharides, the smallest (lower molecular weight) ...
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Pure Appl
Pure may refer to: Computing * A pure function * A pure virtual function * PureSystems, a family of computer systems introduced by IBM in 2012 * Pure Software, a company founded in 1991 by Reed Hastings to support the Purify tool * Pure-FTPd, FTP server software * Pure (programming language), functional programming language based on term rewriting * Pure Storage, a company that makes datacenter storage solutions * Pure (CRIS), a research information system bought by Elsevier. Companies and products * Pure (app), dating app * Pure (restaurant chain), a British fast food chain * Pure Insurance, Privilege Underwriters Reciprocal Exchange * Pure Trading, a Canadian electronic communication network operated by CNQ * Pure Digital, a UK consumer electronics company specialising in DAB radios * Pure Oil, a U.S. chain of gas stations * Propulsion Universelle et Récuperation d'Énergie (PURE), a motorsport engineering company * Pure FM (Portsmouth), a university radio station based in P ...
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Utility
As a topic of economics, utility is used to model worth or value. Its usage has evolved significantly over time. The term was introduced initially as a measure of pleasure or happiness as part of the theory of utilitarianism by moral philosophers such as Jeremy Bentham and John Stuart Mill. The term has been adapted and reapplied within neoclassical economics, which dominates modern economic theory, as a utility function that represents a single consumer's preference ordering over a choice set but is not comparable across consumers. This concept of utility is personal and based on choice rather than on pleasure received, and so is specified more rigorously than the original concept but makes it less useful (and controversial) for ethical decisions. Utility function Consider a set of alternatives among which a person can make a preference ordering. The utility obtained from these alternatives is an unknown function of the utilities obtained from each alternative, not the sum of ...
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Disparlure
''cis''-7,8-Epoxy-2-methyloctadecane (also known as disparlure) is a chemical compound with formula C19H38O. It is a sex pheromone found in moths, such as the spongy moth, and is used to attract a mate. It is also a harmful pesticide for many tree species. Occurrences Disparlure is produced by female moths, such as the spongy and nun moths. It is a sex pheromone, a chemical that is released by the moths in order to attract a male mate. Disparlure has two enantiomers, referred to by (+) and (-). The (+) enantiomer is typically used to attract the males by the females, while the (-) enantiomer tends to have the opposite effect. The (-) enantiomer inhibits attractions and turns the males away from females. Synthesis There are two main ways to synthesize disparlure. They are either using chiral pools, which are costly and time consuming, or asymmetric epoxidation, which is quick, easy, and cheap. Some studies have used asymmetric epoxidation, which involves processes such as constr ...
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Leukotriene
Leukotrienes are a family of eicosanoid inflammatory mediators produced in leukocytes by the oxidation of arachidonic acid (AA) and the essential fatty acid eicosapentaenoic acid (EPA) by the enzyme arachidonate 5-lipoxygenase. Leukotrienes use lipid signaling to convey information to either the cell producing them (autocrine signaling) or neighboring cells (paracrine signaling) in order to regulate immune responses. The production of leukotrienes is usually accompanied by the production of histamine and prostaglandins, which also act as inflammatory mediators. One of their roles (specifically, leukotriene D4) is to trigger contractions in the smooth muscles lining the bronchioles; their overproduction is a major cause of inflammation in asthma and allergic rhinitis. Leukotriene antagonists are used to treat these disorders by inhibiting the production or activity of leukotrienes. History and name The name ''leukotriene'', introduced by Swedish biochemist Bengt Samuelsso ...
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Erythromycin
Erythromycin is an antibiotic used for the treatment of a number of bacterial infections. This includes respiratory tract infections, skin infections, chlamydia infections, pelvic inflammatory disease, and syphilis. It may also be used during pregnancy to prevent Group B streptococcal infection in the newborn, as well as to improve delayed stomach emptying. It can be given intravenously and by mouth. An eye ointment is routinely recommended after delivery to prevent eye infections in the newborn. Common side effects include abdominal cramps, vomiting, and diarrhea. More serious side effects may include ''Clostridium difficile'' colitis, liver problems, prolonged QT, and allergic reactions. It is generally safe in those who are allergic to penicillin. Erythromycin also appears to be safe to use during pregnancy. While generally regarded as safe during breastfeeding, its use by the mother during the first two weeks of life may increase the risk of pyloric stenosis in th ...
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Alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, and Biological Chemistry'. 1232 pages. Two general types of monoalkenes are distinguished: terminal and internal. Also called α-olefins, terminal alkenes are more useful. However, the International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc. for cyclic ones; and "olefin" for the general class – cyclic or acyclic, with one or more double bonds. Acyclic alkenes, with only one double bond and no other functional groups (also known as mono-enes) form a homologous series of hydrocarbons with the general formula with '' ...
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Kinetic Resolution
In organic chemistry, kinetic resolution is a means of differentiating two enantiomers in a racemic mixture. In kinetic resolution, two enantiomers react with different reaction rates in a chemical reaction with a chiral catalyst or reagent, resulting in an enantioenriched sample of the less reactive enantiomer. As opposed to chiral resolution, kinetic resolution does not rely on different physical properties of diastereomeric products, but rather on the different chemical properties of the racemic starting materials. The enantiomeric excess (ee) of the unreacted starting material continually rises as more product is formed, reaching 100% just before full completion of the reaction. Kinetic resolution relies upon differences in reactivity between enantiomers or enantiomeric complexes. Kinetic resolution can be used for the preparation of chiral molecules in organic synthesis. Kinetic resolution reactions utilizing purely synthetic reagents and catalysts are much less common tha ...
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Tetrahedron (journal)
''Tetrahedron'' is a weekly peer-reviewed scientific journal covering the field of organic chemistry. According to the ''Journal Citation Reports'', ''Tetrahedron'' has a 2020 impact factor of 2.457. ''Tetrahedron'' and Elsevier, its publisher, support an annual symposium. In 2010, complaints were raised over its high subscription cost. Notable papers , the Web of Science lists ten papers from ''Tetrahedron'' that have more than 1000 citations. The four articles that have been cited more than 2000 times are: * – cited 2228 times * – cited 2162 times * – cited 2124 times * – cited 2107 times See also * ''Tetrahedron Letters'' * ''Tetrahedron Computer Methodology'' * ''Polyhedron In geometry, a polyhedron (plural polyhedra or polyhedrons; ) is a three-dimensional shape with flat polygonal faces, straight edges and sharp corners or vertices. A convex polyhedron is the convex hull of finitely many points, not all on th ...'' (journal) Refere ...
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