674-26-0Relevant articles and documents
MANUFACTURING METHOD OF β-HYDROXYLACTONE (METH)ACRYLIC ACID ESTER
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Paragraph 0045; 0049-0051, (2020/01/23)
PROBLEM TO BE SOLVED: To provide a method capable of manufacturing (meth)acrylic acid ester of β-hydroxylactone at high yield with almost no side reaction. SOLUTION: The problem is solved by a manufacturing method of β-hydroxylactone (meth)acrylic acid ester for providing corresponding (meth)acrylic acid ester by reacting specific β-hydroxylactone (B) and at least one kind of acid anhydride (C) selected from (meth)acrylic acid anhydride (C1) and anhydride of (meth)acrylic acid and carboxylic acid other than the (meth)acrylic acid (C2) in presence of a specific Lewis acid catalyst (A). SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
Method for preparing mevalonolactone from biosynthesized mevalonic aicd using phosphoric acid
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Paragraph 0038; 0040; 0046, (2018/08/02)
The present invention refers to a method using a phosphoric acid bath disclosure number [...] maul proposal it buys preformed biosynthesis from each other. The present invention refers to any impurities can be obtained have a high purity [...] effect. (by machine translation)
METHODS OF FORMING DIOL COMPOUNDS
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Paragraph 0094, (2017/11/06)
Methods of forming a C4 to C7 diol compound, the methods including a first step of reacting a C4 to C7 dicarboxylic acid with hydrogen (H2) gas on a first heterogeneous catalyst at a first temperature and a first pressure to form a C4 to C7 lactone; and a subsequent step of reacting the lactone with hydrogen (H2) gas on a second heterogeneous catalyst at a second temperature and a second pressure, wherein the second temperature is lower than the first temperature. Also disclosed are methods of forming a solvent, the methods including reacting a C4 to C7 dicarboxylic acid with hydrogen (H2) gas on a first heterogeneous catalyst at a first temperature and a first pressure to form a solvent. Further disclosed herein are methods that include reacting mevalonolactone with hydrogen (H2) gas on a second heterogeneous catalyst at a second temperature and a second pressure to form a diol compound.
PROCESSES FOR CONVERSION OF BIOLOGICALLY DERIVED MEVALONIC ACID
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Paragraph 0094, (2016/06/13)
The invention relates to a process comprising reacting mevalonic acid, or a solution comprising mevalonic acid, to yield a first product or first product mixture, optionally in the presence of a solid catalyst and/or at elevated temperature and/or pressure. The invention further relates to a process comprising: (a) providing a microbial organism that expresses a biosynthetic mevalonic acid pathway; (b) growing the microbial organism in fermentation medium comprising suitable carbon substrates, whereby biobased mevalonic acid is produced; and (c) reacting said biobased mevalonic acid to yield a first product or first product mixture.
Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols
Xie, Xiaomin,Stahl, Shannon S.
, p. 3767 - 3770 (2015/04/14)
Cu/nitroxyl catalysts have been identified that promote highly efficient and selective aerobic oxidative lactonization of diols under mild reaction conditions using ambient air as the oxidant. The chemo- and regioselectivity of the reaction may be tuned by changing the identity of the nitroxyl cocatalyst. A Cu/ABNO catalyst system (ABNO = 9-azabicyclo[3.3.1]nonan-N-oxyl) shows excellent reactivity with symmetrical diols and hindered unsymmetrical diols, whereas a Cu/TEMPO catalyst system (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyl-N-oxyl) displays excellent chemo- and regioselectivity for the oxidation of less hindered unsymmetrical diols. These catalyst systems are compatible with all classes of alcohols (benzylic, allylic, aliphatic), mediate efficient lactonization of 1,4-, 1,5-, and some 1,6-diols, and tolerate diverse functional groups, including alkenes, heterocycles, and other heteroatom-containing groups.
Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)-Verapamil
Oliveira, Caio C.,Pfaltz, Andreas,Correia, Carlos Roque Duarte
supporting information, p. 14036 - 14039 (2016/01/25)
We describe herein a highly regio- and enantioselective Pd-catalyzed Heck arylation of unactivated trisubstituted acyclic olefins to provide all-carbon quaternary stereogenic centers. Chiral N,N ligands of the pyrimidine- and pyrazino-oxazoline class were developed for that purpose, providing the desired products in good to high yields with enantiomeric ratios up to >99:1. Both linear and branched substituents on the olefins were well-tolerated. The potential of this new method is demonstrated by the straightforward synthesis of several O-methyl lactols and lactones containing quaternary stereocenters, together with a concise enantioselective total synthesis of the calcium channel blocker verapamil.
Synthesis of mevalonate-and fluorinated mevalonate prodrugs and their in vitro human plasma stability
Kang, Soosung,Watanabe, Mizuki,Jacobs,Yamaguchi, Masaya,Dahesh, Samira,Nizet, Victor,Leyh, Thomas S.,Silverman, Richard B.
, p. 448 - 461 (2016/10/19)
The mevalonate pathway is essential for the production of many important molecules in lipid biosynthesis. Inhibition of this pathway is the mechanism of statin cholesterol-lowering drugs, as well as the target of drugs to treat osteoporosis, to combat parasites, and to inhibit tumor cell growth. Unlike the human mevalonate pathway, the bacterial pathway appears to be regulated by diphosphomevalonate (DPM). Enzymes in the mevalonate pathway act to produce isopentenyl diphosphate, the product of the DPM decarboxylase reaction, utilize phosphorylated (charged) intermediates, which are poorly bioavailable. It has been shown that fluorinated DPMs (6-fluoro-and 6,6,6-trifluoro-5-diphosphomevalonate) are excellent inhibitors of the bacterial pathway; however, highly charged DPM and analogs are not bioavailable. To increase cellular permeability of mevalonate analogs, we have synthesized various prodrugs of mevalonate and 6-fluoro-and 6,6,6-trifluoromevalonate that can be enzymatically transformed to the corresponding DPM or fluorinated DPM analogs by esterases or amidases. To probe the required stabilities as potentially bioavailable prodrugs, we measured the half-lives of esters, amides, carbonates, acetals, and ketal promoieties of mevalonate and the fluorinated mevalonate analogs in human blood plasma. Stability studies showed that the prodrugs are converted to the mevalonates in human plasma with a wide range of half-lives. These studies provide stability data for a variety of prodrug options having varying stabilities and should be very useful in the design of appropriate prodrugs of mevalonate and fluorinated mevalonates.
A catalytic enantioselective route to hydroxy-substituted quaternary carbon centers: Resolution of tertiary aldols with a catalytic antibody
List, Benjamin,Shabat, Doron,Zhong, Guofu,Turner, James M.,Li, Anthony,Bui, Tommy,Anderson, James,Lerner, Richard A.,Barbas III, Carlos F.
, p. 7283 - 7291 (2007/10/03)
Aldolase antibody 38C2-catalyzed resolutions of tertiary aldols were studied. Tertiary aldols proved to be very good substrates for antibody catalyzed retro-aldol reactions. The catalytic proficiency, (k(cat)/K(M))/k(uncat), of the antibody for these reactions was on the order of 1010 M-1. A fluorogenic tertiary aldol allowed for the quantitative study of enantiomeric excess as a function of reaction conversion, revealing an E value of ca. 160 in this case. Study of a variety of substrates demonstrated that antibody-catalyzed retro-aldolization provides rapid entry to highly enantiomerically enriched tertiary aldols, typically > 95% ee, containing structurally varied, heteroatom-substituted quaternary carbon centers. The utility of this approach to natural product syntheses has been demonstrated with the syntheses of (+)-frontalin, the side chain of Saframycin H, and formal syntheses of (+)- and (-)-mevalonolactone.
Synthesis of lactones via the oxidation of α,ω-diols with sodium bromite and alumina under water free conditions
Hirano, Masao,Yakabe, Shigetaka,Morimoto, Takashi
, p. 123 - 130 (2007/10/03)
Oxidation of α,ω-diols with sodium bromite can be readily performed in dichloromethane to afford lactones in fair good yield under mild and neutral conditions with the aid of chromatographic acidic alumina.
Oxidation of Alcohols with Peracetic Acid in Ethyl Acetate in the Presence of Sodium Bromide
Morimoto, Takashi,Hirano, Masao,Hamaguchi, Takayoshi,Shimoyama, Masahide,Zhuang, Xiumin
, p. 703 - 706 (2007/10/02)
Aliphatic primary alcohols and 1,ω-diols were oxidized to the dimeric esters and lactones, respectively, by peracetic acid in ethyl acetate in the presence of sodium bromide under mild conditions.Aliphatic secondary and benzylic alcohols were converted smoothly to the corresponding carbonyl compounds by the same system.
