Category: 20859-23-8

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reciprocal transformation of optical antipodes, II》. Authors are Walden, P.; Lutz, O..The article about the compound:(S)-2-Bromosuccinic acidcas:20859-23-8,SMILESS:O=C(O)[C@@H](Br)CC(O)=O).SDS of cas: 20859-23-8. Through the article, more information about this compound (cas:20859-23-8) is conveyed.

l-brom, and l-chlor-succinic acids with silver oxid give l-malic acid; heated with alcoholic ammonia, on the other hand, they give rise to d-amino-succinic acid, which on boiling with baryta water gives off ammonia and is converted into the barium salt of d-malic acid.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (S)-2-Bromosuccinic acid( cas:20859-23-8 ) is researched.Computed Properties of C4H5BrO4.Guerin, Philippe; Vert, Michel published the article 《Enantiomeric purity of R(+) and S(-) benzyl malolactonate monomers as determined by 250 MHz 1H nuclear magnetic resonance》 about this compound( cas:20859-23-8 ) in Polymer Communications. Keywords: benzylmalolactonate enantiomeric purity NMR; optical rotation benzyl malolactonate enantiomer; polybenzyl malate enantiomer melting temperature. Let’s learn more about this compound (cas:20859-23-8).

The title studies showed that the enantiomeric excess ≤95% could be retained during the 4-step synthesis route. A linear relation was obtained between optical rotation and enantiomeric composition of mixtures of optical isomers, as determined by NMR and optical polarimetry. Optically active poly(benzyl β-malate) derived from monomer mixtures with R(+)/S(-) ≥70/30 was crystalline and showed a melting temperature that varied with enantiomeric composition

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

SDS of cas: 20859-23-8. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: (S)-2-Bromosuccinic acid, is researched, Molecular C4H5BrO4, CAS is 20859-23-8, about Synthesis and Evaluation of Novel TLR2 Agonists as Potential Adjuvants for Cancer Vaccines. Author is Lu, Benjamin L.; Williams, Geoffrey M.; Verdon, Daniel J.; Dunbar, P. Rod; Brimble, Margaret A..

Cancer immunotherapy has gained increasing attention due to its potential specificity and lack of adverse side effects when compared to more traditional modes of treatment. Toll-like receptor 2 (TLR2) agonists are lipopeptides possessing the S-[2,3-bis(palmitoyloxy)propyl]-L-cysteine (Pam2Cys) motif and exhibit potent immunostimulatory effects. These agonists offer a means of providing “”danger signals”” in order to activate the immune system toward tumor antigens. Thus, the development of TLR2 agonists is attractive in the search of potential immunostimulants for cancer. Existing SAR studies of Pam2Cys with TLR2 indicate that the structural requirements for activity are, for the most part, very intolerable. We have investigated the importance of stereochem., the effect of N-terminal acylation, and homologation between the two ester functionalities in Pam2Cys-conjugated lipopeptides on TLR2 activity. The R diastereomer is significantly more potent than the S diastereomer and N-terminal modification generally lowers TLR2 activity. Most notably, homologation gives rise to analogs which are comparatively active to the native Pam2Cys containing constructs.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Polec, I.; Cieslak, L.; Huras, B.; Nowacka-Krukowska, H.; Sledzinski, B. published an article about the compound: (S)-2-Bromosuccinic acid( cas:20859-23-8,SMILESS:O=C(O)[C@@H](Br)CC(O)=O ).Related Products of 20859-23-8. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:20859-23-8) through the article.

The synthesis of malathion enantiomers and their physicochem. properties were described. Optically active di-Et bromosuccinate isomers, obtained from L- and D-aspartic acid by diazotization in the presence of NaBr followed by esterification with EtOH, were treated in 1,4-dioxane by O,O-di-Me dithiophosphoryl anion, resulting in malathion enantiomers in 50-60% yield. Toxicol. characteristics of these malathion enantiomers were determined by evaluation of the LD50 for some arthropod species and LD50 i. p. for rats.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: (S)-2-Bromosuccinic acid, is researched, Molecular C4H5BrO4, CAS is 20859-23-8, about Stereoselective synthesis of resorcylic acid lactone Cochliomycin B.Quality Control of (S)-2-Bromosuccinic acid.

The total synthesis of 14-membered resorcylic acid lactone, Cochliomycin B (I) has prescribed, in a convergent manner, from readily available starting materials, D-galactose, L-aspartic acid and Et acetoacetate. The key reactions involved in the synthesis are Julia-Kocienski olefination, E-selective Horner-Wadsworth-Emmons olefination and intramol. lactonization.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Bulletin of the Chemical Society of Japan called Optical resolution by preferential crystallization of (RS)-bromosuccinic acid, Author is Shiraiwa, Tadashi; Ohkubo, Masanori; Miyazaki, Hideya; Kubo, Motoki; Nishigawa, Hiroki; Tsujimoto, Toshihiro; Kurokawa, Hidemoto, which mentions a compound: 20859-23-8, SMILESS is O=C(O)[C@@H](Br)CC(O)=O, Molecular C4H5BrO4, Electric Literature of C4H5BrO4.

The racemic structure of (RS)-bromosuccinic acid [(RS)-BSA] was examined based on the melting-point, solubility, IR spectrum, and binary and ternary phase diagrams. The results indicated that (RS)-BSA exists as a conglomerate at room temperature, although it forms a racemic compound at the m.p. The optical resolution by preferential crystallization of (RS)-BSA yielded (R)- and (S)-BSA with optical purities of 81-93%. In addition, (RS)-BSA was optically resolved using (1S,2S)-2-amino-1-phenyl-1,3-propanediol as a resolving agent, to yield (R)- and (S)-BSA with optical purities of 99 and 83%, resp. The obtained (R)- and (S)-BSA were recrystallized from water to obtain optically pure BSA enantiomers.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 20859-23-8, is researched, Molecular C4H5BrO4, about Synthesis of the Griseusin B Framework via a One-Pot Annulation-Methylation-Double Deprotection-Spirocyclization Sequence, the main research direction is griseusin B framework synthesis annulation methylation deprotection spirocyclization.Synthetic Route of C4H5BrO4.

A highly convergent synthesis of the griseusin B scaffold I is described. The key step involves an efficient one-pot Hauser-Kraus annulation-methylation-double deprotection-spirocyclization sequence that directly affords the target parent tetracyclic ring system starting from phthalide II and substituted enone III.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 20859-23-8, is researched, Molecular C4H5BrO4, about An efficient synthesis of enantiomerically pure (R)-(2-benzyloxyethyl)oxirane from (S)-aspartic acid, the main research direction is benzyloxyethyloxirane; oxirane benzyloxyethyl.Synthetic Route of C4H5BrO4.

A 3-step synthesis of the title compound (I) from (S)-aspartic acid (II) is described. Thus, II reacted with NaNO2/KBr to give (S)-(-)bromosuccinic acid which was reduced to (S)-2-bromo-1,4-butanediol (III). III was treated with NaH/THF and PhCH2Br/tetrabutylammonium iodide to give I in 78% yield. The overall yield of this process is 65% and the enantiomeric purity (ep) of the product is greater than 99%.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

COA of Formula: C4H5BrO4. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: (S)-2-Bromosuccinic acid, is researched, Molecular C4H5BrO4, CAS is 20859-23-8, about Synthesis of N4-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine analogs. L-2-chloro-, L-2-bromo-, and D,L-2-methylsuccinamic acid analogs.

L-Chlorosuccinic anhydride, L-bromosuccinic anhydride, and D,L-methylsuccinic anhydride react with 2-acetamido-2-deoxy-β-D-glucopyranosylamine to give varying mixtures of N4-(β-GlcNAc)-2-substituted- and N4-(β-GlcNAc)-3-substituted-succinamic acid isomers. The two regioisomers are separated by anion exchange chromatog. The N4-(β-GlcNAc)-2-substituted-succinamic acid isomers are characterized as analogs of N4-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine.

Compound(20859-23-8)COA of Formula: C4H5BrO4 received a lot of attention, and I have introduced some compounds in other articles, similar to this compound((S)-2-Bromosuccinic acid), if you are interested, you can check out my other related articles.

Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Preparation and biological evaluation of a novel pH-sensitive poly (β-malic acid) conjugate for antitumor drug delivery, published in 2018-12-31, which mentions a compound: 20859-23-8, mainly applied to polymalic acid doxorubicin antitumor drug delivery system, Application of 20859-23-8.

Poly (ss-malic acid), referred to as PMLA, has been synthesized and introduced as a polymeric drug carrier due to its desirable biol. properties. In the present study, a novel pH-sensitive polymer-drug conjugate based on PMLA, PMLA-Hz-doxorubicin (DOX), was prepared, and another conjugate, PMLA-ami-D OX, was synthesized as a comparison. The structures, conjugation efficiency, and drug release properties of the prodrugs were determined The cytotoxicity and cell uptake were assessed using the HT1080 human fibrosarcoma cell line as an in vitro cell model. The release of DOX in the two conjugates were pH-dependent in PBS buffer at a pH of 5.6, 6.0, 6.8 and 7.4. The quantity of drug released increased with the decrease in pH, and PMLA-ami-D OX released twice as much as PMLA-Hz-D OX (12 h). The cytotoxicity of PMLA-Hz-D OX at pH 7.4 was lower than that of free DOX and increased with the decrease in pH, indicating that the cytotoxicity of PMLA-Hz-D OX was pH-sensitive. Flow cytometry and confocal experiments confirmed the efficiency of the PMLA-Hz-D OX conjugate. Therefore, bonding DOX to PMLA via an acid-sensitive hydrazone bond may be used to reduce its toxic side effects on normal tissues while responding to tumor pH and releasing the drug.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”