Category: 20859-23-8

Electric Literature of C4H5BrO4. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: (S)-2-Bromosuccinic acid, is researched, Molecular C4H5BrO4, CAS is 20859-23-8, about Optical resolution of (RS)-mercaptosuccinic acid and syntheses of four stereoisomers of 2-amino-3-[(1,2-dicarboxyethyl)sulfanyl]propanoic acid. Author is Shiraiwa, Tadashi; Ohkubo, Masanori; Kubo, Motoki; Miyazaki, Hideya; Takehata, Masaki; Izawa, Hisashi; Nakagawa, Kazuo; Kurokawa, Hidemoto.

To synthesize four stereoisomers of 2-amino-3-[(1,2-dicarboxyethyl)sulfanyl]propanoic acid (ADC), (RS)-mercaptosuccinic acid [(RS)-MSA] was optically resolved using (1S,2S)-2-amino-1-phenyl-1,3-propanediol and (R)- and (S)-1-phenylethylamine as resolving agents to yield (R)- and (S)-MSA with optical purities of 100%. In addition, the racemic structures of 1-propylammonium and 1-butylammonium salts of (RS)-MSA were examined based on m.p., solubility, IR spectra, and binary and ternary phase diagrams, with the aim of optical resolution by preferential crystallization of (RS)-MSA. Results indicated that the 1-butylammonium salt of (RS)-MSA [(RS)-BA salt] exists as a conglomerate and that the 1-propylammonium salt forms a racemic compound Optical resolution by preferential crystallization of (RS)-BA salt yielded (R)- and (S)-BA salts with optical purities of over 90%. The (R)- and (S)-MSA obtained by optical resolution were condensed with (R)- and (S)-2-amino-3-chloropropanoic acid hydrochlorides to give (2R,1’R)-, (2S,1’S)-, (2R,1’S)-, and (2S,1’R)-ADC. In addition, these stereoisomers were also synthesized from D- and L-cysteine and optically active bromosuccinic acid.

There is still a lot of research devoted to this compound(SMILES：O=C(O)[C@@H](Br)CC(O)=O)Electric Literature of C4H5BrO4, and with the development of science, more effects of this compound(20859-23-8) can be discovered.

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

Recommanded Product: (S)-2-Bromosuccinic acid. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (S)-2-Bromosuccinic acid, is researched, Molecular C4H5BrO4, CAS is 20859-23-8, about Reaction of ammonia with optically active halogenated carboxylic acids supported on anion exchange resin. Author is Urata, Yoshikiyo.

The exchange degrees of Amberlyst A-26 (OH form) treated with L-α-chloro-(I) and L-α-bromosuccinic acid (II) were 70 and 58%, resp., dehydrobromination of II to fumaric acid was also observed L-Aspartic acid, prepared from I via the L-α-chlorosuccinate form of the resin by treatment with NH3-MeOH, aqueous NH3, liquid NH3, and NH3(g) was more optically active than the L-aspartic acid obtained by the direct treatment of I with NH3. The rearrangement during the substitution reaction of NH3 with the L-α-chlorosuccinate form of the resin occurred with configurational retention. The effect of the macro-mol. structure on this reaction was discussed.

There is still a lot of research devoted to this compound(SMILES：O=C(O)[C@@H](Br)CC(O)=O)Recommanded Product: (S)-2-Bromosuccinic acid, and with the development of science, more effects of this compound(20859-23-8) can be discovered.

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

Application of 20859-23-8. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: (S)-2-Bromosuccinic acid, is researched, Molecular C4H5BrO4, CAS is 20859-23-8, about Thiomalate complexes of gold(I): preparation, characterization and crystal structures of 1:2 gold to thiomalate complexes. Author is Leblanc, Daren J.; Smith, Richard W.; Wang, Zhixian; Howard-Lock, Helen E.; Lock, Colin J. L..

The preparation and characterization of 1:2 gold to thiomalate complexes, as ammonium salts, is described. The crystal structures of both racemic and optically pure samples, (NH4)5[AuL2]·H2O [H3L = thiomalic acid, HO2CCH(SH)CH2CO2H] are described and compared. In each case, the gold atom is linearly coordinated to two ligand sulfur atoms. Bond lengths and angles are normal.

There is still a lot of research devoted to this compound(SMILES：O=C(O)[C@@H](Br)CC(O)=O)Application of 20859-23-8, and with the development of science, more effects of this compound(20859-23-8) can be discovered.

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

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 20859-23-8, is researched, SMILESS is O=C(O)[C@@H](Br)CC(O)=O, Molecular C4H5BrO4Journal, Tetrahedron called Copper-catalyzed cross-coupling of amino acid-derived amides with (Z)-vinyl iodides: Unexpected solvent effect and preparation of plocabulin, Author is Wang, Leiming; Lei, Xinsheng; Wang, Quanrui; Li, Yingxia, the main research direction is peptide plocabulin synthesis microtubule destabilizer agent; amino acid amide copper catalyzed cross coupling vinyl iodide.Electric Literature of C4H5BrO4.

A copper-catalyzed cross-coupling reaction of amino acid-derived amides and (Z)-vinyl iodide was studied to improve a key step in the synthesis of plocabulin, a novel microtubule destabilizer agent of marine origin. The study revealed a profound solvent effect with 1,2-dimethoxyethane (DME), which gave consistently high yields across a large variety of the amide and (Z)-vinyl iodide substrates. The protocol was successfully utilized in the preparation of plocabulin and provided a significantly improved yield.

If you want to learn more about this compound((S)-2-Bromosuccinic acid)Electric Literature of C4H5BrO4, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(20859-23-8).

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

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《The Walden rearrangement in the succinic acid group》. Authors are Holmberg, Bror.The article about the compound:(S)-2-Bromosuccinic acidcas:20859-23-8,SMILESS:O=C(O)[C@@H](Br)CC(O)=O).COA of Formula: C4H5BrO4. Through the article, more information about this compound (cas:20859-23-8) is conveyed.

Opinions on the frequency of the Walden inversion (C.A. 5, 2820) have varied all the way from that of Walden himself, who considered the rearrangement as the exception and result of “”abnormal”” reaction, to that of Olson (C.A. 27, 3874), who proposed the theory that rearrangement always accompanies substitution on the asym. C atom. The results of Fredga (C.A. 39, 1392.8), as well as many of the author’s own, support Olson’s thesis in that reactions such as L(-)-HO2CCH2CH(OH)CO2H → PCl5 D(+)-HO2CCH2CHClCO2H, involving only a simple substitution, always cause inversion. Fredga’s “”quasi-racemate”” method was used to establish configurations. Reactions such as esterification of malic acid do not change the optical configuration since they do not effect the asym. C atom. Hydrolysis of L(-)-bromosuccinic acid to either D(+)- or L(-)-malic acids, depending on the means, is explained by the fact that this hydrolysis always proceeds via the D(+)-malic acid β-lactone, which is saponified by either alkali or acid to D(+)-malic acid, leading to the conclusion that the bond broken in saponification is that between the CO2H group and the lactone O. Hydrolysis with H2O alone yields L(-)-malic acid, since the bond from the asym. C atom to the lactone O is in this case broken by addition of the elements of H2O. Thus the pH of the solution is the factor determining which optical antipode of malic acid is formed in the hydrolysis of bromosuccinic acid. Walden’s Ag2O here serves only to further the formation of lactone. Walden’s observation that the presence of Cu++ ions in the hydrolysis causes formation of D(+)-malic acid is explained on the grounds that the Cu complex formed with HO acids has the same catalytic action on hydrolysis as H+ ions. This has been proven for the hydrolysis of acetylated HO acids. However, L(+)-HO2CCH2CH(NH2)CO2H + HONO → L(-)-HO2CCH2CH(OH)CO2H and L(+)-HO2CCH2CH(NH2)CO2H + NOCl → L(-)-HO2CCH2CHClCO2H. Asparagine reacts in analogous fashion, whereas the di-Et L(-)-aspartate yields the D(+)-derivative The diazotization reaction of aspartic acid is therefore the only exception to Olson’s rule. So far it has been impossible to find any intermediate in this reaction that might cause a 2nd optical inversion as in the hydrolysis of bromosuccinic acid. Thus even 1-step reactions on the asym. C atom may not lead to Walden rearrangement, but this must be considered the exception rather than the rule.

If you want to learn more about this compound((S)-2-Bromosuccinic acid)COA of Formula: C4H5BrO4, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(20859-23-8).

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

Robinson, James E.; Brimble, Margaret A. published an article about the compound: (S)-2-Bromosuccinic acid( cas:20859-23-8,SMILESS:O=C(O)[C@@H](Br)CC(O)=O ).Formula: C4H5BrO4. 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 first enantioselective synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine Me ether (I) has been carried out in a convergent fashion by heterocycle-activated Julia olefination of a spiroacetal-containing sulfone fragment with a phthalide-containing aldehyde fragment. The total synthesis of (+)-spirolaxine Me ether establishes the absolute stereochem. of the natural product to be (3R,2”R,5”R,7”R).

Here is a brief introduction to this compound(20859-23-8)Formula: C4H5BrO4, if you want to know about other compounds related to this compound(20859-23-8), you can read my other articles.

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