Tag: 605.6065

Total synthesis and absolute configuration of the natural amino acid tetrahydrolathyrine was written by Benohoud, Meryem;Leman, Loic;Cardoso, Silvia H.;Retailleau, Pascal;Dauban, Philippe;Thierry, Josiane;Dodd, Robert H.. And the article was included in Journal of Organic Chemistry in 2009.Safety of (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide This article mentions the following:

The natural product tetrahydrolathyrine (I) has been synthesized through an iminoiodane-mediated aziridination of a (2S)-allylglycinol derivative, which provided a 2:3 mixture of diastereoisomers. One of these diastereoisomers was converted to the natural product and the other to its C-4 epimer. The C-4 configuration was established from NOESY NMR anal. and X-ray structure of compounds derived from the non-natural diastereoisomer. Thus, the absolute configuration of natural tetrahydrolathyrine was confirmed. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Safety of (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. The development of synthetic approaches for efficient construction of novel quinuclidine derivatives is of great significance. Carbamoyl boranes are generally prepared as adducts with tertiary amines, such as trialkyl amines, pyridine, or quinuclidine, via two synthetic approaches based either on amidation of amine-carboxyborane adducts or on hydrolysis of amine-cyanoboranes.Safety of (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Enantioselective synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester (Vinyl-ACCA-OEt) by asymmetric phase-transfer catalyzed cyclopropanation of (E)-N-phenylmethyleneglycine ethyl ester was written by Belyk, Kevin M.;Xiang, Bangping;Bulger, Paul G.;Leonard, William R.;Balsells, Jaume;Yin, Jingjun;Chen, Cheng-yi. And the article was included in Organic Process Research & Development in 2010.Computed Properties of C37H37BrN2O This article mentions the following:

A concise asym. synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid Et ester, a key intermediate in the preparation of many hepatitis C virus inhibitors, is described. Stereoselective cyclopropanation of (E)-N-phenylmethyleneglycine Et ester was effected by treatment with trans-1,4-dibromo-2-butene in the presence of a catalytic amount of a chiral phase-transfer catalyst. Microscale high-throughput experimentation techniques were successfully used to identify a cinchonidine-derived catalyst that provided (1R,2S)-1-(E)-N-phenylmethyleneamino-2-vinylcyclopropanecarboxylic acid Et ester in up to 84% ee. This was translated to a lab scale process to attain 78% yield and 77.4% ee. Chiral purity upgrade and isolation of the ester was accomplished via preparatory supercritical fluid chromatog. followed by crystallization of the ester as its tosylate salt. The improved synthesis described herein represents a potentially more economical preparation of this valuable intermediate. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Computed Properties of C37H37BrN2O).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. In alkane solvents quinuclidine is a Lewis base that forms adducts with a variety of Lewis acids. Quinuclidine derivatives can also be formed conveniently by introducing substituents into the quinuclidine ring, but the scope of this method is rather limited by the available source of starting materials.Computed Properties of C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Production at the Curie level of no-carrier-added 6-¹⁸F-fluoro-L-dopa was written by Libert, Lionel C.;Franci, Xavier;Plenevaux, Alain R.;Ooi, Takashi;Maruoka, Keiji;Luxen, Andre J.;Lemaire, Christian F.. And the article was included in Journal of Nuclear Medicine in 2013.Product Details of 200132-54-3 This article mentions the following:

6-¹⁸F-fluoro-L-dopa (¹⁸F-FDOPA) has proven to be a useful radiopharmaceutical for the evaluation of presynaptic dopaminergic function using PET. In comparison to electrophilic synthesis, the no-carrier-added (NCA) nucleophilic method has several advantages. These include much higher available activity and specific activity. Recently, we have described an NCA enantioselective synthesis using a chiral phase-transfer catalyst. However, some chems. were difficult to implement into a com. available synthesizer, restricting access to this radiopharmaceutical to only a few PET centers. Methods: In this paper, 2 important chem. improvements are proposed to simplify production of ¹⁸F-FDOPA, resulting in straightforward automation of the synthesis in a com. available module. Results: First, a fast, simple, and reliable synthesis of 2-¹⁸F-fluoro-4,5-dimethoxybenzyl iodide on a solid-phase support was developed. Second, a phase-transfer catalyst alkylation of a glycine derivative at room temperature was used to enable enantioselective carbon-carbon bond formation. After hydrolysis and high-performance liquid chromatog. purification, a high enantiomeric excess of ¹⁸F-FDOPA (鈭?7%) was obtained using a chiral catalyst available from a biphenyl 3 substrate. The total synthesis time was 63 min, and the decay-corrected radiochem. yield was 36% 卤 3% (n = 8). Conclusion: By exploiting the advantages of this NCA approach, using a starting activity of 185 GBq of NCA ¹⁸F-fluoride, high activities of ¹⁸F-FDOPA (>45 GBq) with high specific activity (鈮?53 GBq/渭mol) are now available at the end of synthesis for use in clin. investigations. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Product Details of 200132-54-3).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. In alkane solvents quinuclidine is a Lewis base that forms adducts with a variety of Lewis acids. Quinuclidine derivatives can also be formed conveniently by introducing substituents into the quinuclidine ring, but the scope of this method is rather limited by the available source of starting materials.Product Details of 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Diastereoselective Aziridination of Chiral Electron-Deficient Olefins with N-Chloro-N-sodiocarbamates Catalyzed by Chiral Quaternary Ammonium Salts was written by Murakami, Yuta;Takeda, Youhei;Minakata, Satoshi. And the article was included in Journal of Organic Chemistry in 2011.Application of 200132-54-3 This article mentions the following:

Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the “matching” stereochem. combination of chiral auxiliary/ammonium salt. For example, when 3-phenyl-(4R,7S)-4-methyl-7-isopropyl-4,5,6,7-tetrahydroindazole (L-menthopyrazole) as a chiral auxiliary and a cinchonidine-derived chiral ammonium salt as a catalyst were applied to the reaction system, perfect diastereoselectivity was realized. Furthermore, the preparation of enantiomerically pure aziridines by removal of the chiral auxiliary was demonstrated. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Application of 200132-54-3).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. The configuration at C-8 (quinuclidine attachment) and C-9 position (bearing hydroxy group) are important as they help in the orientation of hydroxy group and nitrogen atom of quinuclidine.Application of 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Enantioselective Phase-Transfer Catalyzed 伪-Sulfanylation of Isoxazolidin-5-ones: An Entry to 尾^2,2-Amino Acid Derivatives was written by Cadart, Timothee;Berthonneau, Clement;Levacher, Vincent;Perrio, Stephane;Briere, Jean-Francois. And the article was included in Chemistry – A European Journal in 2016.COA of Formula: C37H37BrN2O This article mentions the following:

An unprecedented enantioselective 伪-functionalization of C4-substituted N-alkoxycarbonyl isoxazolidin-5-ones, readily available platforms from Meldrum’s acid derivatives, by N-sulfanylphthalimide (PhthSR) electrophiles was achieved upon an efficient phase-transfer catalytic approach, mediated by a com. N-spiro quaternary ammonium catalyst. Two catalytic activities of the in situ formed R₄N⁺Phth^– species were highlighted, the phtalimidate being involved in the anion metathesis event and likely as a Bronsted base. This sequence offers a straightforward access to 伪,伪-disubstituted isoxazolidinones, which turned out to be useful precursors of 伪-sulfanyl-尾^2,2-amino acid derivatives In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3COA of Formula: C37H37BrN2O).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. Asymmetric construction of quinuclidine derivatives has been realized by an iridium-catalyzed allylic dearomatization reaction. The catalytic system, derived from [Ir(cod)Cl]2 and the Feringa ligand, tolerates a broad range of substrates. A large array of quinuclidine derivatives can be obtained under mild conditions in good to excellent yields (68%鈥?6%), diastereoselectivity (up to >20/1 dr), and enantioselectivity (up to >99% ee).COA of Formula: C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Polymeric pseudo-liquid membranes from polymethacrylate derivative bearing oligodimethylsiloxane unit was written by Tsujimoto, Hiroki;Yoshikawa, Masakazu. And the article was included in Journal of Membrane and Separation Technology in 2017.Formula: C37H37BrN2O This article mentions the following:

Novel liquid membrane system, which is named polymeric pseudo-liquid membrane was constructed from polymethacrylate derivative bearing oligodimethylsiloxane (PDMSMA), showing rubbery state under operating conditions, as a membrane matrix. In the present study, dibenzo-18-crown-6 (DB18C6), dibenzo-21-crown-7 (DB21C7) or O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (AMCC) was adopted as a carrier for KCl transport, CsCl transport or optical resolution of racemic mixture of phenylglycine (Phegly), resp. The results of KCl and CsCl transports revealed that the membrane transport was attained by carrier-diffusion mechanism like conventional liquid membranes. The present study led the conclusion that PDMSMA can be applicable not only to membrane transport of alkali metal ions, such as K⁺ and Cs⁺, but also to chiral separation In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Formula: C37H37BrN2O).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. Quinuclidine derivatives are also widely utilized as homogeneous or heterogeneous catalysts in various asymmetric processes such as Morita鈥揃aylis鈥揌illman reactions, Sharpless dihydroxylation reactions, and phase-transfer catalytic reactions. As a ligand, quinuclidine is useful in the studies of OsO4-catalyzed dihydroxylation of olefins. It plays an important role in the formation of onium salts used testing of PAC-antagonist activity.Formula: C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Polymeric pseudo-liquid membranes from poly(octadecyl methacrylate) was written by Tsujimoto, Hiroki;Yoshikawa, Masakazu. And the article was included in Journal of Membrane Science in 2013.SDS of cas: 200132-54-3 This article mentions the following:

The novel liquid membrane system, which is named polymeric pseudo-liquid membrane, was constructed from poly(octadecyl methacrylate) (PC18MA), which showed a rubbery state under operating conditions, as a membrane matrix, and dibenzo-18-crown-6 (DB18C6) for the transport of KCl or O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (AAMC) for that of racemic mixture of phenylglycine (Phegly) as a carrier. The results of KCl transport revealed that KCl transport was attained by carrier-diffusion mechanism even though membrane matrix was composed of polymeric material. The polymeric pseudo-liquid membrane containing chiral carrier AAMC showed optical resolution ability, in other words, the membrane selectively transported L-Phegly and its permselectivity toward L-Phegly reached 1.48 at the operating temperature of 40 掳C. Chiral separation ability was greatly dependent on the operating temperature and a wide range of permselectivity from L-isomer to D-isomer permselectivity was attained by adjusting the operating temperature The present study revealed that the polymeric pseudo-liquid membrane is a promising membrane system in membrane separation In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3SDS of cas: 200132-54-3).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. It is employed to prepare quinine and alkaloids. Carbamoyl boranes are generally prepared as adducts with tertiary amines, such as trialkyl amines, pyridine, or quinuclidine, via two synthetic approaches based either on amidation of amine-carboxyborane adducts or on hydrolysis of amine-cyanoboranes.SDS of cas: 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Nucleophilic enantioselective synthesis of 6-fluoro-L-dopa via chiral catalytic phase-transfer alkylation was written by Tang, Ganghua;Tang, Xiaolan;Zhang, Lan;Wang, Yongxian. And the article was included in Zhongguo Yaowu Huaxue Zazhi in 2002.Formula: C37H37BrN2O This article mentions the following:

6-Fluoro-L-dopa was synthesized from 6-nitropiperonal via nucleophilic fluorination, reductive iodination, chiral catalytic phase-transfer alkylation, and hydrolysis reactions. The enantiomeric purity of 6-fluoro-L-dopa was determined by HPLC method using a chiral mobile phase and reversed-phase C₁₈ column. The overall yield from 6-nitropiperonal was 38%, and enantiomeric purity of 6-fluoro-L-dopa was above 95%. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Formula: C37H37BrN2O).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. Quinuclidine is found as a structural component of some biomolecules including quinine. The reactions of quinuclidine compounds that lead to opening of the 1-azabi-cyclic system at the N-C and C-C bonds to give piperidine derivatives or, via subsequent rearrangements, derivatives of other heterocyclic systems, are correlated.Formula: C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Organocatalytic Regio- and Asymmetric C-Selective S_NAr Reactions-Stereoselective Synthesis of Optically Active Spiro-pyrrolidone-3,3′-oxoindoles was written by Bella, Marco;Kobbelgaard, Sara;Jorgensen, Karl Anker. And the article was included in Journal of the American Chemical Society in 2005.Product Details of 200132-54-3 This article mentions the following:

The first example of catalytic enantioselective nucleophilic aromatic substitution of 尾-dicarbonyl compounds is presented. An O-benzoylated cinchona alkaloid derivative catalyst gave a selective C-arylation reaction compared to, e.g., the corresponding benzylated catalyst which provided a 1:1 mixture of the C- and O-arylation products. The reaction proceeds well for various aromatic compounds with different 1,3-dicarbonyl compounds, and the optically active products are obtained in very high yields and with up to 92% ee. One further scope of this reaction is demonstrated by the synthesis of the optically active spiro-pyrrolidone-3,3′-oxoindole structure. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Product Details of 200132-54-3).

(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. Quinuclidine is found as a structural component of some biomolecules including quinine. Carbamoyl boranes are generally prepared as adducts with tertiary amines, such as trialkyl amines, pyridine, or quinuclidine, via two synthetic approaches based either on amidation of amine-carboxyborane adducts or on hydrolysis of amine-cyanoboranes.Product Details of 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider