cas 100836-85-9, (R)-(+)-2-BENZYLOXYPROPIONIC ACID

Articles about 100836-85-9Total 35 be found

Article title
Article abstract
Author
Journal number and time
Download

Developing Pd(II) catalyzed double sp3 C-H alkoxylation for synthesis of symmetric and unsymmetric acetals
An effective Pd(II) catalyzed double unactivated C(sp3)-H alkoxylation has been developed to prepare both symmetric and unsymmetric acetals. This new reaction demonstrates good functional group tolerance, excellent reactivity, and high yields. A variety of novel acetals can be readily accessed via this new method. (Chemical Equation Presented).
Zong, Yu,Rao, Yu
p. 5278 - 5281
(2014)
Read Online

HPLC separation of 2-aryloxycarboxylic acid enantiomers on chiral stationary phases
The possibility for separating enantiomers of a number of practically significant 2-aryloxycarboxylic acids was studied by normal- and reversed-phase HPLC on popular chiral stationary phases. The best separation parameters were achieved on the chiral phases with the polysaccharide base Chiralcel OD-H and Chiralpack AD under the normal-phase HPLC conditions. The (S)- and (R)-enantiomers of 2-(1-naphthyloxy)- and 2-(2-iodophenoxy)propionic acids with enantiomeric excess ee >99% were isolated using preparative chiral HPLC.
Charushin, V. N.,Chulakov, E. N.,Krasnov, V. P.,Levit, G. L.,Sadretdinova, L. Sh.,Tumashov, A. A.,Vakarov, S. A.
p. 900 - 907
(2021/06/07)

Synthesis method of (R)-2-benzyloxypropionic acid and intermediate thereof
The invention relates to the technical field of organic synthesis, in particular to a synthesis method of (R)-2-benzyloxypropionic acid and an intermediate thereof. The synthesis method of the intermediate for synthesizing (R)-2-benzyloxypropionic acid comprises the step of adding sodium tert-amyl alcohol into a reaction system of R-methyl lactate and benzyl halogen. According to the synthesis method, the raw materials are easy to obtain and cheap, the production cost can be reduced, meanwhile, flammable, explosive and harmful gas cannot be formed in the reaction process, the safety risk is greatly reduced, and large-scale safety production is facilitated.
-
Paragraph 0038-0066

(2021/08/11)

Casein kinase 1[epsilon] inhibitor, pharmaceutical composition and application thereof
The invention discloses a novel substituted pyrazolopyrimidine compound for inhibiting the activity of casein kinase 1[epsilon] (CK1[epsilon]), a stereoisomer or a stereoisomer mixture of the novel substituted pyrazolopyrimidine compound, a pharmaceutically acceptable salt or solvate of the novel substituted pyrazolopyrimidine compound, and application of the compound to preparation of medicine for treating diseases, disorders or symptoms benefiting from the inhibition of the activity of casein kinase 1[epsilon] (CK1[epsilon]). The compound has inhibitory activity on CK1[epsilon] kinase, OCI-LY10 cells and Karpas299 cells, shows good anti-tumor activity in an OCI-LY10 subcutaneous xenogeneic model, shows excellent synergistic anti-tumor activity when being combined with a BTK inhibitor, has good pharmacokinetic properties, and can be applied to treatment of diseases, disorders or symptoms, including cancers, autoimmune diseases and the like, which benefit from inhibition of casein kinase 1[epsilon] activity, alone or in combination with other drugs.
-
(2021/01/11)

Acyclic 1,4-Stereocontrol via the Allylic Diazene Rearrangement: Development, Applications, and the Essential Role of Kinetic e Stereoselectivity in Tosylhydrazone Formation
We report full details of a method for 1,3-reductive transposition of α-alkoxy-α,β-unsaturated hydrazones to provide E-alkenes with high 1,4-stereocontrol between the two respective allylic stereocenters. The process couples a chelation-controlled reduction of the hydrazone with an in situ allylic strain controlled retro-ene reaction of an allyl diazene, i.e., an allylic diazene rearrangement. Such stereotriads are frequently observed motifs in natural products. We observed a fortuitous kinetic preference for the E-hydrazone geometry during the hydrazonation reaction, as only the E-isomers could undergo chelation-controlled reduction.
Shrestha, Maha L.,Qi, Wei,McIntosh, Matthias C.
p. 8359 - 8370
(2017/08/23)

COMPOUNDS FOR USE IN TREATING NEUROMUSCULAR DISORDERS
The present invention relates to compositions comprising compounds for use in treating, ameliorating and/or preventing neuromuscular disorders. The compounds as defined herein preferably inhibit the ClC-1 ion channel. The invention further relates to methods of treating, preventing and/or ameliorating neuromuscular disorders, by administering said composition to a person in need thereof.
-
Page/Page column 103; 104

(2017/01/02)

COMPOUNDS, COMPOSITIONS, AND METHODS FOR INCREASING CFTR ACTIVITY
The disclosure encompasses compounds having e.g., Formula (la) or (lb), compositions thereof, and methods of modulating CFTR activity. The diclosure also encompasses methods of treating a condition associated with CFTR activity or condition associated with a dysfunction of proteostasis comprising administering to a subject an effective amount of a compound of Formula (I) or (lb).
-
(2015/10/05)

Divergent Synthesis of Aeruginosins Based on a C(sp3)￡H Activation Strategy
A general and scalable access to the aeruginosin family of marine natural products, exhibiting potent inhibitory activity against serine proteases, is reported. This was enabled by the strategic use of two recently implemented Pd-catalyzed C(sp3)￡H activation reactions. The first method allowed us to obtain the common 2-carboxy-6-hydroxyoctahydroindole (Choi) core of the target molecules on a large scale, whereas the second method provided a rapid and divergent access to various hydroxyphenyllactic (Hpla) subunits, including halogenated ones. This unique strategy, together with an optimization of the fragment coupling sequence allowed the synthesis of four aeruginosins, that is, 98A-C and 298A from the chiral pool. Among them, aeruginosin 298A was synthesized on an unprecedentedly large scale. In addition, halogenated aeruginosins 98A and 98C were synthesized for the first time, thanks to a fine-tuning of the final hydrogenation step. Go natural! A general and scalable access to the aeruginosin family of marine natural products (see graphic), exhibiting potent inhibitory activity against serine proteases, is described. The strategic use of two different Pd-catalyzed C(sp3)￡H activation reactions led to the synthesis of aeruginosins98A-C and 298A.
Dailler, David,Danoun, Grégory,Ourri, Benjamin,Baudoin, Olivier
p. 9370 - 9379
(2015/06/30)

A general and scalable synthesis of aeruginosin marine natural products based on two strategic C(sp3)-H activation reactions
An efficient and scalable access to the aeruginosin family of marine natural products, which exhibit potent inhibitory activity against serine proteases, is reported. This synthesis was enabled by the strategic use of two different, recently implemented C(sp3)-H activation reactions. The first method led to the common 2-carboxy-6-hydroxyoctahydroindole (Choi) core of the target molecules on a large scale, whereas the second one provided rapid and divergent access to the various hydroxyphenyllactic (Hpla) subunits. This strategy allowed the synthesis of the aeruginosins 98B and 298A, with the latter being obtained in unprecedentedly large quantities.
Dailler, David,Danoun, Grégory,Baudoin, Olivier
p. 4919 - 4922
(2015/04/14)

Catalytic enantioselective inverse electron demand hetero-diels-alder reaction with allylsilanes
The first diastereo- and enantioselective inverse electron demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters with allylsilanes is described. Chiral copper(II) catalysts successfully activate the β,γ-unsaturated α-ketoesters and promote the reaction with allylsilanes with excellent enantioselectivities. This process represents a new entry to chiral oxanes.
Matsumura, Yuki,Suzuki, Takahiro,Sakakura, Akira,Ishihara, Kazuaki
p. 6131 - 6134
(2014/06/23)

Process for the Preparation of Triazole Antifungal Drug, Its Intermediates and Polymorphs Thereof
A process for the preparation of 4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-ylmethyl)-3-furanyl]methoxy]phenyl]-1-piperazinyl]phenyl]-2-[(1S,2S)-1-ethyl-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one compound of formula-1, its intermediates and polymorphs thereof. (I)
-
Paragraph 0328

(2014/12/09)

Enantioselective protonation of α-hetero carboxylic acid-derived ketene disilyl acetals under chiral ionic Bronsted acid catalysis
Highly enantioselective protonation of α-halo and alkoxy carboxylic acid-derived ketene disilyl acetals is achieved by using P-spiro chiral diaminodioxaphosphonium barfate as a Bronsted acid catalyst, where the enantiofacial discrimination by the catalyst mainly stems from the recognition of the electronic difference between two substituents on the ketene disilyl acetal.
Uraguchi, Daisuke,Kizu, Tomohito,Ohira, Yuki,Ooi, Takashi
p. 13489 - 13491
(2015/01/09)

Synthesis and biological evaluation of 3,7-diazabicyclo[4.3.0]nonan-8-ones as potential nootropic and analgesic drugs
A series of cis and trans 3,7-diazabicyclo[4.3.0]nonan-8-ones has been synthesized and tested for their ability to revert scopolamine-induced amnesia in the mouse passive-avoidance test. The racemates of the most potent compounds 4 and 7 were separated and tested, but no enantioselectivity was found for the nootropic activity. Compounds 4 and 7 and their enantiomers displayed interesting antihyperalgesic activity in two models of neuropathic pain (streptozotocin-induced and oxalilplatin-induced neuropathy) in comparison with pregabalin.
Martini, Elisabetta,Di Cesare Mannelli, Lorenzo,Bartolucci, Gianluca,Bertucci, Carlo,Dei, Silvia,Ghelardini, Carla,Guandalini, Luca,Manetti, Dina,Scapecchi, Serena,Teodori, Elisabetta,Romanelli, Maria Novella
supporting information; experimental part
p. 2512 - 2516
(2011/06/24)

Highly diastereoselective α-hydroxylation of fox chiral auxiliary-based amide enolates with molecular oxygen
"Figure Presented" Using a trifluoromethylated oxazolidine (Fox) chiral auxiliary, the hydroxylation reaction of enolates was very efficiently performed under smooth and friendly conditions with molecular oxygen as oxidizer. This reaction occurred with an extremely high diastereoselectivlty. After cleavage, the chlral auxiliary Is efficiently recovered and highly valuable enantlopure oxygenated carboxylic acids and alcohols are released.
Lubin, Hodney,Tessier, Arnaud,Chaume, Gregory,Pytkowicz, Julien,Brigaud, Thierry B.
supporting information; experimental part
p. 1496 - 1499
(2010/07/03)

Diastereoselective alkylation of chiral 2-imidazolidinone glycolates: Asymmetric synthesis of α-hydroxy carboxylic acids
Sodium enolates of chiral 2-imidazolidinone glycolates reacted with alkyl halides to produce α-alkylated products with high diastereoselectivities, which were readily removed by simple alkaline hydrolysis and were converted to the protected α-hydroxy carboxylic acids. The new stereogenic center was assigned the (R)-configuration by comparison with known compounds.
Chong, Chul Chun,Lee, Gue-Jae,Jae, Nyoung Kim,Taek, Hyeon Kim
p. 2989 - 2992
(2007/10/03)

Microbial deracemization of α-substituted carboxylic acids: Substrate specificity and mechanistic investigation
A new enzymatic method for the preparation of optically active α-substituted carboxylic acids is reported. This technique is called deracemization reaction, which provides us with a route to obtain the enantiomerically pure compounds, theoretically in 100% yield starting from the racemic mixture. This means that the synthesis of a racemate is almost equal to the synthesis of the optically active compound, and this concept is entirely different from the commonly accepted one in the asymmetric synthesis. Using the growing cell system of Nocardia diaphanozonaria JCM3208, racemates of 2-aryl- and 2-aryloxypropanoic acid are deracemized smoothly and (R)-form-enriched products are recovered in high chemical yield (>50%). In addition, using optically active starting compounds and deuterated derivatives as well as inhibitors, we have disclosed the fact that a new type of enzyme takes part in this biotransformation, and that the reaction proceeds probably via the same mechanism as that in rat liver.
Kato, Dai-Ichiro,Mitsuda, Satoshi,Ohta, Hiromichi
p. 7234 - 7242
(2007/10/03)

Process for the preparation of 2-hydroxyalkyl halophenones
2-Benzyloxyalkyl halophenones of the formula (3): wherein X1and X2are each independently H, Cl or F, provided that at least one of X1and X2is Cl or F; one of R3and R4is H and the other is optionally substituted benzyloxy; and R5is an unsubstituted alkyl, preferably a C1-6alkyl group. The compounds are useful as intermediates for preparing 2-hydroxyalkyl halophenones.
-
Example 1

(2010/01/31)

Non-carbonyl-stabilized metallocarbenoids in synthesis: The development of a tandem rhodium-catalyzed bamford-stevens/thermal aliphatic claisen rearrangement sequence
A tandem rhodium-catalyzed Bamford-Stevens/Claisen rearrangement is presented. The tandem reaction uses Eschenmoser hydrazones for the in situ generation of non-carbonyl-stabilized diazo alkanes, which are presumably intercepted by Rh(II) catalysts to induce a 1,2-hydride migration. This sequence provides high levels of stereocontrol for the generation of simple acyclic (Z)-enol ethers. These enol ethers undergo either thermal or Lewis acid accelerated Claisen rearrangements to provide products of high diastereopurity. Also presented are cascade reactions, wherein a third chemical step occurs after the initial tandem sequence (i.e., Bamford-Stevens/Claisen/ene and Bamford-Stevens/Claisen/Cope). Copyright
May, Jeremy A.,Stoltz, Brian M.
p. 12426 - 12427
(2007/10/03)

An inexpensive carbohydrate derivative used as a chiral auxiliary in the synthesis of α-hydroxy carboxylic acids
Protected α-hydroxy carboxylic acids were synthesized in moderate yield and high diastereoselectivity by alkylation of glycolate (α-hydroxy acetate) enolates using a D-fructose-derived chiral auxiliary. The new chiral center was assigned the R configuration based on comparisons of optical rotations and on one crystal structure analysis. This alkylation methodology is compatible with several hydroxyl protecting groups. The free hydroxy acids were obtained upon removal of the protecting group from the hydroxyl functionality followed by saponification.
Yu, Hongwu,Ballard, C.Eric,Boyle, Paul D,Wang, Binghe
p. 7663 - 7679
(2007/10/03)

A highly stereoselective entry to α-hydroxy carboxylic acids using D-fructose diacetonide as a chiral auxiliary
Protected α-hydroxy carboxylic acids were synthesized in moderate yield and high diastereoselectivity by alkylation of glycolate ester enolates using a D-fructose-derived chiral auxiliary. The new chiral center was assigned the (R)-configuration based upon comparisons to the literature. Both enantiomers of the auxiliary are readily available.
Yu, Hongwu,Ballard, C. Eric,Wang, Binghe
p. 1835 - 1838
(2007/10/03)

Process for the preparation of 2-hydroxyalkyl halophenones
A process is provided for the preparation of compounds of Formula (1): wherein X1and X2are each independently H, Cl or F, provided that at least one of X1and X2is Cl or F; one of R1and R2is H and the other is OH; and R5is an unsubstituted alkyl, preferably a C1-6alkyl, group. The process comprises condensing a 2-chloroalkanoic acid with an optionally substituted benzyl alcohol to form a 2-(optionally substituted benzyloxy) alkanoic acid, converting the condensation product to the corresponding acid chloride and then either reacting the acid chloride with a compound of the Formula (2) in the presence of a source of copper (I) to give a compound of Formula (3) wherein one of R3and R4is H and the other is optionally substituted benzyloxy; or reacting the acid chloride with a compound of Formula (4): A—NH—B wherein A and B independently represent substituted alkyl, alkoxy, aryl or oxyaryl groups, or are linked to form a heterocyclic ring to form an amide, and then reacting the amide with a compound of Formula (2) to give a compound of Formula (3). The optionally substituted benzyl group from the compound of Formula (3) can removed by hydrogenation.
-
(2008/06/13)

Towards the semi-synthesis of didemnin M. solution and solid phase synthesis of the pseudotetrapeptide: pGlu-Glnψ[COO]Ala-Pro-OH
Two approaches, solution and solid phase syntheses, were developed for the synthesis of the pseudotetrapeptide, pGlu-Glnψ[COO]Ala-Pro-OH. Both approaches gave comparable synthetic yields, but the latter approach provided an expedient entry to the synthesis of the target compound with higher product purity.
Wen, James J.,Crews, Craig M.
p. 779 - 782
(2007/10/03)

Useful for treating neurodegenerative diseases
Novel benzomorphan derivatives of the formula STR1 wherein R1 -R8 are as defined herein. The benzomorphan derivatives are useful for treating cerebral ischaemia of various origins, epilepsy and neurodegenerative diseases.
-
(2008/06/13)

Preparation of (R)-(+)-Lithium Lactate
Optically pure (R)-(+)-lithium lactate (7) and its benzyl ether analogue (6a) were obtained from acetaldehyde using Eliel's 1,3-trans-oxathiane (1) as the chiral auxiliary for chromatographic separation.
Cervantes-Cuevas,Joseph-Nathan
p. 201 - 206
(2007/10/03)

THE STUDIES OF METAL ION CATALYZED CARBON-HYDROGEN INSERTION OF α-ALKOXY-α'-DIAZOKETONES DERIVED FROM MANDELIC AND LACTIC ACIDS
The cupric acetylacetonate is the best catalyst to induce the carbon-hydrogen inserted reaction for the α-alkoxy-α'-diazoketones derivatives (5 and 6).The side reactions such as aromatic carbon-hydrogen insertion and rearrangement could be prevented.
Hon, Yung-Son,Chang, Rong-Chi,Chau, Tay-Yuan
p. 1745 - 1750
(2007/10/02)

Total synthesis of erythronolide A
-
Nakata,Arai,Tomooka,Ohsawa,Kinoshita
p. 2618 - 2635
(2007/10/02)

EASY AND GENERAL METHOD TO SYNTHESIZE CHIRAL 2-HYDROXYACID BENZOATES
The synthesis of 2-hydroxyacid benzoates, with high yields and excellent enantioselectivity, by regioselective opening of chiral 2,3-epoxyalcohols and ruthenium dioxide oxidation, is described.
Martin, V. S.,Nunez, M. T.,Tonn, C. E.
p. 2701 - 2702
(2007/10/02)

Synthesis of Analogues of 1,3-Dihydroxyacetone Phosphate and Glyceraldehyde 3-Phosphate for Use in Studies of Fructose-1,6-diphosphate Aldolase
This paper describes the synthesis of five analogues of dihydroxyacetone phosphate (3-azidohydroxyacetone 1-phosphate (5), 3-(acetylamino)hydroxyacetone 1-phosphate (12), (R)-1,3-dihydroxy-2-butanone 1-phosphate (18), (+/-)-1,3-dihydroxy-2-butanone 3-phosphate (26), and phosphonomethyl glycolate (31)).The syntheses of 18 and 26 are based on a new reaction: that is, the introduction of the phosphate group by the reaction of a diazo ketone with dibenzyl phosphate.These methods provide easy access to a number of compounds that are potential substrates for the synthetically useful enzyme aldolase (fructose-1,6-diphosphate aldolase from rabbit muscle, EC 4.1.2.13, RAMA) and perhaps for other enzymes of glycolysis.This paper also describes syntheses of 14 aldehydes for examination as substrates for aldolase.When the precursor was available, ozonolysis of vinyl groups proved to be the best route to the corresponding aldehydes.
Bischofberger, Norbert,Waldmann, Herbert,Saito, Tohru,Simon, Ethan S.,Lees, Watson,et al.
p. 3457 - 3465
(2007/10/02)

SYNTHETIC STUDIES OF ERYTHROMYCINS. II. ENANTIOSPECIFIC SYNTHESIS OF A C-10-C-13 SEGMENT OF ERYTHRONOLIDE A FROM D-RIBOSE
(3R,4R,5R)-5-O-Benzyl-2-iodo-3,4-O-isopropylidene-4-methyl-1-heptene-3,4,5-triol 3, a C-10-C-13 synthetic segment of erythronolide A (1) was enantiospecifically synthesized in sixteen steps and 8.3percent overall yield from D-ribose.
Kinoshita, Mitsuhiro,Arai, Masayuki,Tomooka, Katsuhiko,Nakata, Masaya
p. 1811 - 1814
(2007/10/02)

Antidepressant 1,2,4-triazolone compounds
2-[3-[4-(3-Halophenyl)-1-piperazinyl]propyl]-5-(1-hydroxyethyl)-2,4-dihydro-[4-phenoxyalkyl-3H-1,2,4-triazol-3-ones and closely related compounds are psychotropic agents having promise as antidepressants by virtue of their receptor site binding affinity profiles and animal pharmacology.
-
(2008/06/13)

MICROBIAL REDUCTION OF 2-PHENYLPROPIONIC ACID, 2-BENZYLOXYPROPIONIC ACID AND 2-(2-FURFURYL)PROPIONIC ACID
Racemic 2-phenylpropionic acid and 2-benzyloxypropionic acid were subjected to microbial reduction and simultaneous resolution with several molds. i. e., Malus and Prunus strains of Glomerella cingulata, Gloeosporium olivarum and Gloeosporium laeticolor, yielding (R)-2-phenylpropanol and (S)-2-benzyloxypropanol , and leaving (R)-2-phenylpropionic acid , respectively.The microbial reduction of racemic 2-(2-furfuryl)propionic acid gave optically inactive (+/-)-2-(2-furfuryl)propanol .Keywords- asymetric reduction; 2-benzyloxypropionic acid; 2-(2-furfuryl)prioionic acid; microbial reduction; microbial resolution; 2-phenylpropionic acid
Tsuda, Yoshiko,Kawai, Ken-Ichi,Nakajima, Shoichi
p. 4657 - 4661
(2007/10/02)

A HIGHLY EFFECTIVE ASYMMETRIC SYNTHESIS OF α-HYDROXY ACIDS BY ALKYLATION OF CHIRAL N-(BENZYLOXYACETYL)-TRANS-2,5-BIS(METHOXYMETHOXYMETHYL)PYRROLIDINE
Alkylation of lithiated N-(benzyloxyacetyl)-trans-2,5-bis(methoxymethoxymethyl)-pyrrolidine proceeded with high stereoselectivity (>96percent de) and subsequent transformations of the alkylated products gave synthetically useful α-benzyloxy acids or α-hydroxy acids of high enantiomeric purity.
Enomoto, Masayuki,Ito, Yoshio,Katsuki, Tsutomu,Yamaguchi, Masaru
p. 1343 - 1344
(2007/10/02)

Photolysis of Alkoxyacetic Acids in the presence of Mercury(II) Oxide and Iodine
Homolytic decarboxylation of a series of alkoxyacetic acids has furnished alkoxyalkyl alkoxyacetates when no substituents were present at the 2-position.Electron donating and withdrawing 2-substituents, with the exception of trichloromethyl, afforded products due to fragmentation of the alkoxyacetic acids.The reaction pathway is rationalised on the basis of the reactivity of the alkoxyalkyl iodide intermediates.
Glover, Stephen A.,Golding, Stephen L.,Goosen, Andre,McCleland, Cedric W.
p. 2479 - 2483
(2007/10/02)

Cyclol Formation from Tripeptides containing β-Alanine
Attempts to synthesize stable tetrahedral intermediates (cyclols) from β-alanine containing precursors are described.Cyclization of N-(N-benzyloxycarbonyl-β-alanyl)-Phe-Pro-ONp gave N-(N-benzyloxycarbonyl-β-alanyl)-cyclo-(Phe-D-Pro).Cyclization of N-(N-benzyloxycarbonyl-Ala)-βAla-Pro-ONp and of N--Pro-ONp afforded the corresponding anhydrocyclols.The first example of an oxa-cyclol related to a ten membered cyclodepsitripeptide was synthesized by acylating cyclo-(βAla-Pro) with α-benzyloxypropionyl chloride followed by hydrogenolytic removal of the O-benzyl protecting group.
Pinnen, Francesco,Zanotti, Giancarlo,Lucente, Gino
p. 1311 - 1316
(2007/10/02)