Category: 617-55-0

Daley, Christopher J. A.; Wiles, Jason A.; Bergens, Steven H. published the artcile< Application of [Ru((R)-BINAP)(MeCN)(1-3:5,6-η-C8H11)](BF4) as a catalyst precursor for enantioselective hydrogenations>, COA of Formula: C6H10O5, the main research area is methyl methylbutanoate methylbutanoic acid enantioselective preparation; acetylphenylalanine enantioselective preparation; methylsuccinic acid methyl ester methylsuccinate enantioselective preparation; citronellol enantioselective preparation; ethyl hydroxybutanoate enantioselective preparation; malic acid methyl ester enantioselective preparation; ruthenium BINAP precursor enantioselective hydrogenation; nonracemic ruthenium BINAP catalyst precursor enantioselective hydrogenation; acetone acetonitrile solvate ruthenium BINAP catalyst; enantioselectivity unsaturated acid hydrogenation triethylamine dependence ruthenium BINAP catalyst; unsaturated ester acid hydrogenation enantioselectivity ruthenium BINAP catalyst; ketone hydrogenation enantioselectivity ruthenium BINAP catalyst; substrate dicarboxylate enantioselectivity hydrogenation ruthenium BINAP catalyst.

A catalyst system employing [Ru((R)-BINAP)(MeCN)(1-3:5,6-η5-C8H11)](BF4) (I) as a catalyst precursor was evaluated using the enantioselective hydrogenations of tiglic acid, α-acetamidocinnamic acid, itaconic acid, Me tiglate, di-Me itaconate, geraniol, Et acetoacetate, and di-Me oxaloacetate as a series of typical substrates. Acetone and MeOH were used as model aprotic and protic solvents, resp. The hydrogenation of substrates containing an α,β-unsaturated carboxylic acid functionality required stoichiometric quantities of NEt3 to occur at reasonable rates in acetone solution, while in MeOH solution it did not. The enantioselectivities were typically higher in acetone than in MeOH. This catalyst system is among the more enantioselective ruthenium-BINAP type systems reported for the catalytic hydrogenation of substrates containing an α,β-unsaturated acid or ester functionality. E.g., the hydrogenation of MeO2CC(:CH2)CH2CO2Me in acetone without Et3N under 4 atm H2 with I gave (S)-MeO2CCH(Me)CH2CO2Me with 100% conversion and in 95% ee. The enantioselectivities for the hydrogenation of ketones ranged from poor (15%) to moderate (74%). 1,4-Dicarboxylate substrates with the prochiral olefin or ketone at the 2-position were all hydrogenated in good to high ee with the same enantioface selectivity both with our system and other catalysts reported in the literature. This raised the possibility that these substrates were hydrogenated through intermediates with similar structural features.

Canadian Journal of Chemistry published new progress about Hydrogenation catalysts, stereoselective. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, COA of Formula: C6H10O5.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Nakatani, Shingo; Ikura, Masahiro; Yamamoto, Shingo; Nishita, Yoshitaka; Itadani, Satoshi; Habashita, Hiromu; Sugiura, Tsuneyuki; Ogawa, Koji; Ohno, Hiroyuki; Takahashi, Kanji; Nakai, Hisao; Toda, Masaaki published the artcile< Design and synthesis of novel metalloproteinase inhibitors>, Electric Literature of 617-55-0, the main research area is benzoyl aminobutyrate hydroxamate preparation metalloproteinase inhibitor SAR.

A series of N-benzoyl 4-aminobutyric acid hydroxamate analogs were synthesized and evaluated as matrix metalloproteinase inhibitors. Synthetic work was focused on the chem. modification of the 4-aminobutyric acid part using easily available starting materials. As such, chem. modification was carried out using com. available starting materials such as 4-aminobutyric acid, (+)- and (-)-malic acid, and D- and L-glutamic acid derivatives Among the compounds tested, N-[4-(benzofuran-2-yl)benzoyl] 4-amino-4S-hydroxymethylbutyric acid hydroxamates derived from L-glutamic acid demonstrated more potent inhibitory activity against MMP-2 and MMP-9 compared with the corresponding 2S-hydroxy analogs or 3S-hydroxy analogs, resp., which were derived from (-)-malic acid. Structure-activity relationship study is presented.

Bioorganic & Medicinal Chemistry published new progress about Structure-activity relationship. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Electric Literature of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Zhu, Sheng; Lin, Wen-qing; Zhang, Xiao-mei published the artcile< Process improvement on the synthesis of (S)-(+)-3-hydroxytetrahydrofuran>, SDS of cas: 617-55-0, the main research area is process improvement synthesis hydroxy THF preparation; tetrahydrofuranol preparation asym synthesis.

A method for the synthesis of the title compound [i.e., (S)-(+)-3-hydroxytetrahydrofuran] is reported here. Said target compound (overall yield 43.2%, 99.0% enantiomeric excess) was prepared by a synthetic sequence involving the esterification of L-malic acid, reduction and cyclization through intramol. dehydration. The product structure was determined by NMR.

Hecheng Huaxue published new progress about Cyclization. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, SDS of cas: 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Salvatore, Ralph N.; Chu, Feixia; Nagle, Advait S.; Kapxhiu, Elona A.; Cross, Richard M.; Jung, Kyung Woon published the artcile< Efficient Cs2CO3-promoted solution and solid phase synthesis of carbonates and carbamates in the presence of TBAI>, Product Details of C6H10O5, the main research area is carbamate carbonate preparation cesium carbonate tetrabutylammonium iodide; solid phase preparation carbamate carbonate; carbon dioxide reaction alc amine alkyl halide.

Novel solution and solid-phase methods for the synthesis of carbonates and carbamates were developed using cesium bases and TBAI via a three-component coupling. Cesium carbonate not only promoted successful carbonylations of alcs. and carbamations of amines, but also suppressed common side reactions traditionally seen using existing protocols. Various alcs. and amines were examined, using a wide array of alkyl halides, and the results demonstrated that this methodol. was highly chemoselective. In particular, use of either sterically demanding substrates or amino acid derivatives afforded the corresponding products exclusively, offering a wide variety of applications such as novel protecting groups and peptidomimetic syntheses.

Tetrahedron published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Product Details of C6H10O5.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Madry, Tomasz; Czapik, Agnieszka; Kwit, Marcin published the artcile< Optical Activity and Helicity Enhancement of Highly Sensitive Dinaphthylmethane-Based Stereodynamic Probes for Secondary Alcohols>, Quality Control of 617-55-0, the main research area is optical activity helicity enhancement dinaphthylmethane stereodynamic probe secondary alc.

The chirality transfer from CD-silent secondary alc. (inductor) to the stereodynamic bichromophoric di(1-naphthyl)methane probe (reporter) led to the generation of intense induced exciton-type Cotton effects in the UV/VIS absorption region. The di(1-naphthyl)methane probe exhibits extraordinarily high sensitivity to even small structural variations of the alc. skeleton, i.e., the probe is able to distinguish between an oxygen atom and a methylene group in a 3-hydroxytetrahydrofurane skeleton. Signs and amplitudes of the exciton couplets of 1Bb electronic transition might be correlated with the type of stereo differentiating parts of the mol., flanking the stereogenic center, however, not with the absolute configuration. The origin of the induced Cotton effects was established by means of exptl. and theor. methods. As a result, a mechanism of chirality transfer from permanent stereogenic center to the bichromophore is proposed.

ACS Omega published new progress about Bond angle, dihedral. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Quality Control of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Lowe, Gordon; Potter, Barry V. L. published the artcile< Synthesis, absolute configuration, and circular dichroism of the enantiomers of fluorosuccinic acid>, Reference of 617-55-0, the main research area is malate ester stereospecific fluorination; fluorosuccinate configuration CD; succinate fluoro configuration CD; asym preparation fluorosuccinate.

D-labeling showed that fluorination of (2S)- and (2R)-MeO2CCH(OH)CH2CO2Me with Et2NSF3 (CHCl3, 0éŽ?ambient temperature) occurred stereospecifically with inversion of configuration to give (2R)- and (2S)-MeO2CCHFCH2CO2Me, resp., (I, II, resp.). The CD spectra of I and II and the corresponding acids, obtained by acid hydrolysis, were ‘anomalous’, showing that the previously determined (Harper, D. B., Blakeley, E. R.; 1971) absolute configuration of (+)-HO2CCHFCH2CO2H obtained from Pseudomonal is incorrect.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about Circular dichroism. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Reference of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Qiu, You-Chun; Zhang, Fu-Li; Zhang, Chun-Nian published the artcile< A practical and efficient procedure for reduction of carboxylic acids and their derivatives: use of KBH4-MgCl2>, Category: esters-buliding-blocks, the main research area is carboxylic acid ester anhydride imide reduction borohydride magnesium chloride.

The use of KBH4-MgCl2 to reduce carboxylic acids and their derivatives to the corresponding alcs. or the resp. reduced products is described. Me (S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate used as a reference substrate was reduced with KBH4 and MgCl2 in 1:1 mol ratio to 80 % (S)-1,2-O-isopropylidene-1,2,4-butanetriol. KBH4-LiCl gave higher yields but LiCl is more expensive than MgCl2.

Tetrahedron Letters published new progress about Alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Category: esters-buliding-blocks.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Gao, Mengyu; Sun, Deli; Gong, Hegui published the artcile< Ni-Catalyzed Reductive C-O Bond Arylation of Oxalates Derived from æµ?Hydroxy Esters with Aryl Halides>, Electric Literature of 617-55-0, the main research area is synthesis aryl ester reductive cross coupling oxalate aryl halide; aryl ester preparation arylation aryl halide oxalate radical fragmentation; oxalate radical fragmentation reduction potential.

A Ni-catalyzed reductive cross-coupling of æµ?hydroxycarbonyl compounds modified with oxalyl groups and aryl halides has been developed that furnishes æµ?aryl esters under mild conditions and tolerates a variety of functionalized aryl halides bearing electron-withdrawing and -donating groups. This work highlights C-O bond fragmentation on secondary alkyl carbon centers that generates æµ?carbonyl radicals.

Organic Letters published new progress about Aryl iodides Role: RCT (Reactant), RACT (Reactant or Reagent). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Electric Literature of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Sefkow, Michael; Koch, Andreas; Kleinpeter, Erich published the artcile< New results on the stereoselective alkylations of malic acid derivatives supported by molecular modeling>, Application In Synthesis of 617-55-0, the main research area is stereoselective alkylation malic acid derivative mol modeling.

The stereoselectivity of the alkylation of dialkyl malates is dependent on steric hindrance of both ester alkyl groups. It was found that the two alkyl groups have opposite effects on diastereoselectivity. Increased steric hindrance at the C(1) carboxy group increases the anti-selectivity, whereas increased steric hindrance at the C(4) carboxy group decreases it. The results are explained by comparing the structures of the enolates, which were obtained by mol. modeling. Alkylation at C(4′) of dioxolanones, derived from benzyl-substituted malic acids, with an addnl. stereogenic center on the side chain is dependent on the stereogenic centers of the ring acetal and of the side chain. Alkylation at low temperatures occurs only with cis-dioxolanones having an (R)-configured side-chain stereogenic center. The corresponding trans-dioxolanone and the cis-dioxolanone with a (S)-configured side-chain stereogenic center were recovered unchanged. A rationale is presented with models of monolithiated dioxolanones obtained by ab initio calculations

Helvetica Chimica Acta published new progress about Acetals, cyclic Role: PEP (Physical, Engineering or Chemical Process), RCT (Reactant), PROC (Process), RACT (Reactant or Reagent) (of malic acid derivatives). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Application In Synthesis of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Nakatani, Shingo; Ikura, Masahiro; Yamamoto, Shingo; Nishita, Yoshitaka; Itadani, Satoshi; Habashita, Hiromu; Sugiura, Tsuneyuki; Ogawa, Koji; Ohno, Hiroyuki; Takahashi, Kanji; Nakai, Hisao; Toda, Masaaki published the artcile< Design and synthesis of novel metalloproteinase inhibitors>, Electric Literature of 617-55-0, the main research area is benzoyl aminobutyrate hydroxamate preparation metalloproteinase inhibitor SAR.

A series of N-benzoyl 4-aminobutyric acid hydroxamate analogs were synthesized and evaluated as matrix metalloproteinase inhibitors. Synthetic work was focused on the chem. modification of the 4-aminobutyric acid part using easily available starting materials. As such, chem. modification was carried out using com. available starting materials such as 4-aminobutyric acid, (+)- and (-)-malic acid, and D- and L-glutamic acid derivatives Among the compounds tested, N-[4-(benzofuran-2-yl)benzoyl] 4-amino-4S-hydroxymethylbutyric acid hydroxamates derived from L-glutamic acid demonstrated more potent inhibitory activity against MMP-2 and MMP-9 compared with the corresponding 2S-hydroxy analogs or 3S-hydroxy analogs, resp., which were derived from (-)-malic acid. Structure-activity relationship study is presented.

Bioorganic & Medicinal Chemistry published new progress about Structure-activity relationship. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Electric Literature of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics