Category: 20859-23-8

Narala, Siva Ganesh; Nagalatha, G.; Venkat Narsaiah, A. published the article 《Stereoselective total synthesis of C2-symmetric natural products pyrenophorol and its derivatives》. Keywords: pyrenophorol stereoselective synthesis regioselective epoxide opening reduction Pinnick oxidation; Mitsunobu dilactonization pyrenophorol stereoselective synthesis; CBS reduction; Macrodiolide; Pinnick oxidation; antimicrobiol agent; dilactonization.They researched the compound: (S)-2-Bromosuccinic acid( cas:20859-23-8 ).Recommanded Product: 20859-23-8. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:20859-23-8) here.

A stereoselective total synthesis of 16-membered C2-sym. macrodiolide pyrenophorol (I, R = H), tetrahydropyrenophorol (II) and 4,4-diacetylpyrenophorol I (R = COMe) have been accomplished. The synthesis started from com. available L-Aspartic acid and the key reactions involved are regioselective epoxide opening, CBS reduction, Pinnick oxidation and Mitsunobu dilactonization.

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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, Chromatographia called Super/subcritical fluid chromatography separations with four synthetic polymeric chiral stationary phases, Author is Han, X.; Berthod, A.; Wang, C.; Huang, K.; Armstrong, D. W., the main research direction is supercritical fluid chromatog amide containing polymer silica chiral phase; subcritical fluid chromatog amide containing polymer silica chiral phase.Category: copper-catalyst.

New synthetic polymeric chiral selectors were developed recently as chiral stationary phases. They were tested with supercritical fluid mobile phases made of CO2 plus an alc. modifier and 0.2% volume/volume trifluoroacetic acid. The polymeric N,N’-(1S,2S)-1,2-cyclohexanediyl-bis-2-propenamide (P-CAP), the polymeric N,N’-[(1R,2R)-1,2-diphenyl-1,2-ethanediyl] bis-2-propenamide (P-CAP-DP), the polymeric trans-9,10-dihydro-9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide (DEABV) and the polymeric N,N’-[(1R,2R)-1,2-diphenyl-1,2-ethanediyl] bis-4-vinylbenzamide (DPEVB) were bonded to 5 μm silica particles and used to prepare four columns that were tested with a set of 88 chiral compounds with a wide variety of chem. functionalities. All 88 test compounds were separated on one or more of these related polymeric CSPs. Forty-three enantiomeric pairs were separated in SFC conditions by only one of the CSPs. Twenty pairs were separated by two CSPs and 18 and 7 enantiomeric pairs were separated by 3 and all 4 CSPs, resp. The three P-CAP, P-CAP-DP and DEABV CSPs have equivalent success being able to sep. 49 enantiomeric pairs of the studied set with resp. 12, 14 and 20 at baseline (Rs > 1.5). The DPEVB CSP was significantly less efficient separating only 18 chiral compounds with only one at baseline. The great advantage of the SFC mobile phases is the rapid separation, which most achieved in <5 min. Compounds in my other articles are similar to this one((S)-2-Bromosuccinic acid)Category: copper-catalyst, you can compare them to see their pros and cons in some ways,such as convenient, effective and so on.

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

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.Touet, Joel; Ruault, Thierry; Brown, Eric researched the compound: (S)-2-Bromosuccinic acid( cas:20859-23-8 ).Synthetic Route of C4H5BrO4.They published the article 《Resolving agents. Part 1. (R)-(-)-2-Amino-1-benzyloxybutane, a new base for the resolution of racemic acids》 about this compound( cas:20859-23-8 ) in Synthetic Communications. Keywords: aminobenzyloxybutane resolution carboxylic acid. We’ll tell you more about this compound (cas:20859-23-8).

Treatment of the readily available (R)-(-) enantiomer of 2-aminobutan-1-ol with sodium hydride followed by benzyl chloride afforded (R)-(-)-H2NCHEtCH2OCH2Ph. The latter was successfully used for the resolution of racemic HO2CCHRCH2CO2H (R = Ph, Me, Br) as well as racemic I (Y = H, OMe).

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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 《Stereochemical studies. XXIV. Stereoisomeric (benzoylmercapto)succinic and (benzoylmercapto)succinamic acids》. 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).HPLC of Formula: 20859-23-8. Through the article, more information about this compound (cas:20859-23-8) is conveyed.

cf. C.A. 35, 5465.3. BzSH (6.9 g.) and 5.8 g. maleic acid in hot AcOH yield 7.6 g. DL-HCO2CH(SBz)CH2CO2H (I), m. 177-82°. L(-)-HCO2CH(SBz)CH2CO2H, sintering 175° and m. 182-3°, [α]D20 -6°, [α]D20 -123° (c 0.5028, Me2CO), [M]D20 -315°, was prepared from BzSH, Na2CO3, and L(-)-CHBr(CO2H)CH2CO2H (II) in H2O, while the D(+)-isomer (III), m. 176-80°, [α]D20 6°, [α]D20 124° (c 0.5028, Me2CO), [M]D20 315°, results from the same starting materials when alc.-H2O, and no Na2CO3 is used. III with concentrated NH4OH yields BzNH2 and some dithiodimalic acid, m. 164-6°, [α]D20 257° (Me2CO). PhCSNH2 and II in EtOAc yield PhC(NH2Br)SCH(CO2H)CH2CO2H, m. 205°, with foaming; this in turn is converted by heating in H2O to S.CPh:N.CO.CHCH2CO2H, m. 195-7°. From DL-NH2COCHICH2CO2H with Na2CO3 and BzSH in H2O was prepared DL-BzSCH(CO2H)CH2CONH2, m. 174-5°, while the D(+)-isomer (IV), m. 164-5°, [α]D20 105°, [M]D20 266°, was prepared from L(-)-NH2COCHBrCH2CO2H and BzSK in Na2CO3 solution The free acid, HSCH(CO2H)CH2CONH2 m. 115-16°, [α]D20 84° (c 0.4, Me2CO), was prepared by treating IV with concentrated NH4OH, distilling in vacuo, and acidifying with H2SO4. The course of these reactions may be explained by the mechanisms proposed by Fredga (The Svedberg-Buch 1944, p. 261).

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

Recommanded Product: (S)-2-Bromosuccinic acid. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (S)-2-Bromosuccinic acid, is researched, Molecular C4H5BrO4, CAS is 20859-23-8, about The divergent asymmetric synthesis of kalafungin, 5-epi-frenolicin B and related pyranonaphthoquinone antibiotics. Author is Donner, Christopher D..

A divergent, asym. method for the synthesis of pyranonaphthoquinones is reported. The synthetic strategy applies a Staunton-Weinreb annulation between substituted ortho-toluates and the (R)-pyran-2-one I to construct the key naphthopyranone intermediates, e.g., II. Stereoselective introduction of either a Me or Pr C5 alkyl substituent by use of Grignard addition/silane-mediated reduction and a sequence of oxidations gave a series of pyranonaphthoquinones including kalafungin (III), 5-epi-frenolicin B (IV; R1 = Pr-n, R2 = H), and 5-epi-9-methoxykalafungin (IV; R1 = Me, R2 = OMe).

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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.Application of 20859-23-8.Robinson, James E.; Brimble, Margaret A. published the article 《Synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether and the unnatural (2”S)-diastereomer》 about this compound( cas:20859-23-8 ) in Organic & Biomolecular Chemistry. Keywords: asym synthesis spirolaxine methyl ether Julia Kocienski olefination lactonization; spirocyclization asym synthesis methylspirolaxine mol structure absolute configuration. Let’s learn more about this compound (cas:20859-23-8).

The first enantioselective synthesis of the anti-Heliocbacter pylori agent (+)-spirolaxine Me ether (I) has been carried out in a convergent fashion establishing that the absolute stereochem. of the natural product is in fact (3R, 2”R, 5”R, 7”R) after initial synthesis of the unnatural (2”S)-diastereomer. The key step in the synthesis of (+)-spirolaxine Me ether involved a heterocycle-activated Julia-Kocienski olefination between benzothiazole-based spiroacetal sulfone II and phthalide aldehyde. (2”R, 5”S, 7”S)-spiroacetal sulfone II was prepared via cyclization of a protected dihydroxyketone, which in turn was derived from the coupling of the acetylide derived from a (R)-acetylene with phthalide aldehyde. Phthalide aldehyde was prepared via intramol. acylation of a bromocarbamate III, which was available via titanium tetrafluoride-(+)-BINOL-mediated allylation of 3,5-dimethoxybenzaldehyde. Union of the sulfone II and phthalide aldehyde fragments successfully completed the enantioselective synthesis of I. The synthesis of the unnatural (3R, 2”S, 5”R, 7”R)-diastereomer of I was also undertaken in a similar manner by union of phthalide aldehyde with (2”S, 5”S, 7”S)-spiroacetal sulfone derived from the (S)-acetylene.

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

Related Products of 20859-23-8. 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 Stereoselective total synthesis of obolactones and 7′,8′-dihydroobolactones. Author is Saini, Deepak; Kumar, Praveen; Fernandes, Rodney A..

A concise stereoselective total synthesis of two diastereomeric obolactones and 7′,8′-dihydroobolactones has been achieved using a metal-free catalytic δ-hydroxyalkynone rearrangement, which could provide the required dihydro-γ-pyrone moiety. The desired first stereogenic center was installed through the chiral pool material, L-aspartic acid. Next, the allylation reaction was strategically utilized to provide the requisite olefin bond for the intended ring-closing metathesis, allowing the installation of the remaining dihydro-α-pyrone moiety in the natural products. It also enabled the targeting of both dihydro-α-pyrone diastereomers. Thus, the first stereoselective total synthesis of (+)-7′,8′-dihydroobolactone was accomplished, establishing its structure and absolute configuration.

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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 Optical rotatory dispersion and absolute configuration. Part 20. Chiroptical properties of α-substituted succinic acids. Conformation and absolute configuration, published in 1977, which mentions a compound: 20859-23-8, mainly applied to CD conformation succinate, Synthetic Route of C4H5BrO4.

The effect of conformational preference on the chiroptical properties of α-substituted succinic acids and esters was studied using variable temperature CD in solvents of different polarity. When R1 in the ester RO2CCH2CHR1CO2R (I) is alkyl or halogen, the preferred conformation is II (X = H, Y = R1, Z = CH2CO2R) with the CH2CO2R group eclipsed by the CO bond, whereas when R1 in I is OH, OMe, or NH2, the major conformer is II (X = CH2CO2R, Y = H, Z = R1), in which the heteroatom is eclipsed by the CO bond. In both cases, conformation II (X = R1, Y = CH2CO2R, Z = H) is least favored, mainly on steric grounds. The results when R1 = Cl or Br in I do not support previously proposed conclusions (Listowsky, I. et al., 1970) and an alternative explaination is given. In the resultant octant projection, the sign of the Cotton effect for I will be determined by the position of the groups X and Y in the back octants, and since one of these is always H in the 2 favored conformations, the sign is actually determined by the position of the other group. The octant projection predicts successfully the sign of the ellipticity of the n→π* transition for any α-substituted succinic acid or ester with the appropriate substituent R1, and applied also to simple alkanoic acids and esters with the same substituents.

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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 The stereoselective total synthesis of (3R,5R)-sonnerlactone and (3R,5S)-sonnerlactone.Recommanded Product: (S)-2-Bromosuccinic acid.

The stereoselective synthesis of (3R,5R)-sonnerlactone (I) and (3R,5S)-sonnerlactone has been accomplished starting from l-aspartic acid. Our strategy involves asym. allylation, Alder-Rickert reaction and Mitsunobu macrolactonization as the key steps.

From this literature《The stereoselective total synthesis of (3R,5R)-sonnerlactone and (3R,5S)-sonnerlactone》,we know some information about this compound(20859-23-8)Recommanded Product: (S)-2-Bromosuccinic acid, but this is not all information, there are many literatures related to this compound(20859-23-8).

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

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.Guerin, Philippe; Vert, Michel; Braud, Christian; Lenz, Robert W. researched the compound: (S)-2-Bromosuccinic acid( cas:20859-23-8 ).Synthetic Route of C4H5BrO4.They published the article 《Optically active poly(β-malic acid)》 about this compound( cas:20859-23-8 ) in Polymer Bulletin (Berlin, Germany). Keywords: polymalic acid optical activity; polybenzyl malate hydrolysis. We’ll tell you more about this compound (cas:20859-23-8).

Optically active benzyl malolactonate  [99494-21-0] was prepared starting from L-aspartic acid  [56-84-8] and polymerized anionically using Et3N as initiator to yield poly(benzyl β-malate) [99438-25-2] which is an optically active, semicrystalline polymer. Cleavage of protecting benzyl ester groups yielded optically active poly(β-malic acid) [99438-26-3] which showed 1 accessible pos. CD band in the far UV.

There is still a lot of research devoted to this compound(SMILES：O=C(O)[C@@H](Br)CC(O)=O)Synthetic Route 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”