- Synthesis method 2- hydroxyl carboxylic ester (by machine translation)
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The method, is simple 2 - energy consumption, energy consumption is low, the production :(1) of waste water can be greatly reduced, the yield of the target product is high 2 - and the production cost ;(2) is greatly reduced (1). 2 - The method comprises the following steps, preparing 2 - hydroxycarboxylate, with an acid ;(3) by a byproduct ammonium salt (2) in step, and filtering the excess acid, to remove the byproduct ammonium salt, to obtain 2 - hydroxyl carboxylic acid ester product, by esterification reaction in step (, and filtering to remove 2 - the excess, alcohol), from, the reaction, solution obtained by the reaction solution; of the catalyst under the, action of, a catalyst, to obtain the product of the compound. (by machine translation)
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Paragraph 0052; 0054; 0055; 0058-0060
(2020/05/05)
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- Preparation method of 2-hydroxy acid ester
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The invention relates to a preparation method of 2-hydroxy acid ester and belongs to the technical field of organic synthesis. According to the preparation method of 2-hydroxy acid ester, 2-hydroxy alkyl cyanogens is taken as a raw material to be added to a reaction solution formed by hydrogen chloride, alcohol and water, and after reaction, 2-hydroxy acid ester is obtained. According to the preparation method of 2-hydroxy acid ester, use of a large amount of nonpolar solvent is not needed, and a target product can be obtained by a one-pot method, thus lowering production cost, improving production efficiency and the purify of the target product, and having energy-saving and environment-friendly effects.
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- Asymmetric transfer hydrogenation of α-azido acrylates
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The asymmetric transfer hydrogenation of α-azido acrylates has been explored, a range of α-hydroxy esters are produced with good enantioselectivities (80-90% ee). The reaction was conducted in the wet HCO2H/NEt3 with Ru-TsDPEN A.
- Ji, Yang,Xue, Ping,Ma, Dan-Dan,Li, Xue-Qiang,Gu, Peiming,Li, Rui
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supporting information
p. 192 - 194
(2015/02/05)
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- Biocatalytic racemization of α-hydroxycarboxylic acids using a stereo-complementary pair of α-hydroxycarboxylic acid dehydrogenases
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Biocatalytic racemization of aliphatic, (aryl)aliphatic and aromatic α-hydroxycarboxylic acids was achieved via a reversible oxidation-reduction sequence using a pair of stereo-complementary Prelog- and anti-Prelog d- and l-α-hydroxyisocaproate dehydrogenases from Lactobacillus confusus DSM 20196 and Lactobacillus paracasei DSM 20008, resp., overexpressed in Escherichia coli. The mild reaction conditions ensured essential 'clean' isomerization, undesired 'over-oxidation' of the substrate forming the α-ketoacid could be suppressed by exclusion of O2 and adjustment of the NAD+/NADH-ratio.
- Bodlenner, Anne,Glueck, Silvia M.,Nestl, Bettina M.,Gruber, Christian C.,Baudendistel, Nina,Hauer, Bernhard,Kroutil, Wolfgang,Faber, Kurt
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experimental part
p. 7752 - 7755
(2009/12/04)
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- PROCESS FOR PRODUCTION OF 2-HYDROXY ESTERS
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The invention provides an easy and simple process for the production of 2-hydroxy esters from cyanohydrins, specifically, a process for the production of 2-hydroxy esters represented by the general formula (1) (exclusive of ethyl 2-hydroxy-4-phenylbutyrate), characterized by introducing an acid into a mixture comprising a cyanohydrin represented by the general formula (2), an alcohol, an organic solvent and water: [Chemical formula 1] R1 -CH(OH)-COOR2 (1) R1 -CH(OH)(CN) (2) wherein R1 is hydrogen, a substituted or unsubstituted aliphatic hydrocarbon group which has 1 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen, a substituted or unsubstituted alicyclic hydrocarbon group which has 3 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen, or a substituted or unsubstituted aryl or aralkyl group which has 3 to 14 carbon atoms and may contain oxygen, sulfur, or nitrogen; and R2 is alkyl which has 1 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen.
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Page/Page column 14
(2010/11/30)
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- Bromolysis and iodolysis of α,β-epoxycarboxylic acids in water catalyzed by indium halides
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The ring opening of α,β-epoxycarboxylic acids by bromide and iodide ions has been efficiently carried out in water in high regio- and stereoselective fashion. The iodolysis of trans-β-monoalkylated epoxycarboxylic acids at pH 4.0 was completely α-regioselective and anti diastereoselective. The InCl3-catalyzed iodolysis of a variety of α,β-epoxycarboxylic acids at pH 1.5 gave the corresponding anti β-iodohydrins in 88-95% yields. The one-pot synthesis of the α- and β-hydroxyhexanoic acids, starting from the corresponding α,β-epoxycarboxylic acid 1a by iodolysis followed by reduction of the resulting iodohydrins 4a and 4b by NaBH4-InCl3 in water, has been performed.
- Amantini,Fringuelli,Pizzo,Vaccaro
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p. 4463 - 4467
(2007/10/03)
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- Hydroxynitrile lyase catalyzed enantioselective HCN addition to O-protected α-hydroxyaldehydes
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Various O-protected glycol- and racemic lactaldehydes 3 and 6 as well as O-allyl protected racemic α-hydroxyaldehydes 7 (R1=Et, Pr, Bu) have been prepared to investigate and perform a stereoselective Kiliani-Fischer synthesis by hydroxynitrile lyase (HNL) catalyzed addition of HCN. From all protecting groups investigated the allyl moiety was most suitable. (R)-PaHNL from bitter almonds (Prunus amygdalus), yielding the (2S)-cyanohydrins 8-10, was found to be a more stereoselective catalyst than (S)-MeHNL from maniok (Manihot esculenta). While (R)-PaHNL led to enantiomeric excesses ≥93%, with (S)-MeHNL the (2R)-cyanohydrins 8-10 were obtained with enantiomeric excesses ≤78%.
- Roos, Juergen,Effenberger, Franz
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p. 2817 - 2828
(2007/10/03)
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- Oxidation of α-acetoxy acetals with trichloroisocyanuric acid
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α-Acetoxy acid methyl esters are prepared in excellent yields by treating aliphatic α-acetoxy dimethyl acetals with trichloroisocyanuric acid in DMF.
- Benincasa,Grandi,Ghelfi,Pagnoni
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p. 3463 - 3470
(2007/10/03)
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- High Diastereoselection in the Aldol Reaction of the Bistrimethylsilyl Enol Ether of Methyl Acetoacetate with 2-Benzyloxyhexanal: Synthesis of (-)-Pestalotin
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Aldol condensation of the bistrimethylsilyl enol ether of methyl acetoacetate, compound 2, with 2-benzyloxyhexanal 3c affords highly selectively (99:1) the syn-aldol adduct 4c in the presence of titanium tetrachloride.The stereocontrolled synthesis of (-)-pestalotin 7 has been achieved.
- Hagiwara, Hisahiro,Kimura, Katsuhiko,Uda, Hisashi
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p. 693 - 700
(2007/10/02)
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- Oxygenation of Silyl Enol Ethers and Silyl Ketene Acetals with Molecular Oxygen and Aldehyde Catalyzed by Nickel(II) Complex. A Convenient Method for the Preparation of α-Hydroxy Carbonyl Compounds
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In the presence of a catalytic amount of nickel(II) complex, silyl enol ethers and silyl ketene acetals are smoothly oxygenated by the combined use of molecular oxygen and aldehyde to afford α-siloxy carbonyl compounds via possible intermediates, siloxy epoxides.And on treatment of the α-siloxy carbonyl compounds with potassium fluoride α-hydroxy carbonyl compounds are obtained in good to high yields.
- Takai, Toshihiro,Yamada, Tohru,Rhode, Oliver,Mukaiyama, Teruaki
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p. 281 - 284
(2007/10/02)
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- An Efficient Method for the Direct Peroxygenation of Various Olefinic Compounds with Molecular Oxygen and Triethylsilane Catalyzed by a Cobalt(II) Complex
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An efficient method for the direct peroxygenation of various olefinic compounds with molecular oxygen and triethylsilane (Et3SiH) was developed by the use of a catalytic amount of a bis(1,3-diketonato)cobalt(II) complex.According to the above method, 1-phenyl-3-triethylsilyldioxybutane (2) was directly produced from 4-phenyl-1-butene (1) by means of a reaction with O2 and Et3SiH at room temperature.Styrene (3) and ethyl acrylate (5a) were also smoothly peroxygenated to give 1-phenyl-1-triethylsilyldioxyethane (4) and ethyl 2-triethylsilyldioxypropionate (6a) by using a small amount of t-BuOOH as an initiator.The successive desilylation of 6a and reduction of the resulting ethyl 2-hydroperoxypropionate (8a) afforded the corresponding alcohol, ethyl lactate (10a), in a high yield.The synthetic utility of the present peroxygenation reaction was demonstrated in the preparation of α-hydroxy esters 10a-e from several α,β-unsaturated esters 5a-e via the corresponding triethylsilyldioxy derivatives.
- Isayama, Shigeru
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p. 1305 - 1310
(2007/10/02)
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- Synthesis of S-Methyl 2-Hydrxyalkanethioates, 2-Hydroxyalkanoic Acids and Related Compounds via the Addition Reaction of Tris(methylthio)methanide Ion to Alkanals
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In connection with the studies on biological activities on myrmicacin and related compounds, the synthetic method for 2-hydroxyalkanoic acids and the corresponding 1,2-diols was studied.The addition reaction of tris(methylthio)methyllithium to the aldehydes (propanal-dodecanal) gave the corresponding 1,1,-tris(methylthio)-2-alkanols 1a-j.Treatment of 1 with mercury(II) chloride-mercury(II) oxide in water-acetone afforded S-methyl 2-hydroxyalkanethioates 2a-j, and in methanol methyl 2-hydroxyalkanoates 3c-j were obtained.Reduction of the thioates 2 with lithium aluminium hydride gave 1,2-diols 4c-j and saponification produced the corresponding 2-hydroxyalkanoic acids 5c-j.
- Orito, Kazuhiko,Seki, Yoshikatsu,Suginome, Hiroshi,Iwadare, Tsukasa
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p. 2013 - 2017
(2007/10/02)
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