Tag: 605.6065

Total Synthesis of Tryprostatin B: Synthesis and Asymmetric Phase-Transfer-Catalyzed Reaction of Prenylated Gramine Salt was written by Huisman, Matthew;Rahaman, Mizzanoor;Asad, Sharif;Oehm, Sarah;Novin, Sherwin;Rheingold, Arnold L.;Hossain, M. Mahmun. And the article was included in Organic Letters in 2019.SDS of cas: 200132-54-3 This article mentions the following:

A concise and efficient total synthesis of microtubule inhibitor tryprostatin B is described. The key step is the preparation of a diprenylated gramine salt. In this step, the prenyl group is incorporated at the 2-position of the indole moiety by direct lithiation of the Boc-protected gramine. We also developed and optimized the asym. phase-transfer-catalyzed reaction with the diprenylated gramine salt to provide the C2-prenyl tryptophan intermediate resulting in 93% enantiomeric excess (ee) and 65% yield. The total synthesis of tryprostatin B is done in six steps with 35% overall yield. 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. The development of synthetic approaches for efficient construction of novel quinuclidine derivatives is of great significance. 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.SDS of cas: 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Free radical-mediated aryl amination: a practical synthesis of (R)- and (S)-7-azaindoline 伪-amino acid was written by Srinivasan, Jayasree M.;Burks, Heather E.;Smith, Colin R.;Viswanathan, Rajesh;Johnston, Jeffrey N.. And the article was included in Synthesis in 2005.Electric Literature of C37H37BrN2O This article mentions the following:

Two nonnatural proline derivatives, (S)- and (R)-7-azaindoline 伪-amino acids I, have been prepared and isolated as their trifluoroacetate salts on gram scale. The convergent sequence (6 steps from 2-bromopyridine) employs phase transfer-catalyzed asym. alkylation of Ph₂C:NCH₂CO₂Bu-t with 3-bromomethyl-2-bromopyridine to give (S)- and (R)-2-[N-(diphenylmethylene)amino]-3-(2-bromo-3-pyridyl)propanoates II, followed by their free radical-mediated aryl amination leading to cyclization. Implementation of the solid-liquid phase transfer conditions requires manual pulverization of CsOH, efficient mech. stirring, and effective low temperature control. This large scale free radical cyclization protocol replaces benzene solvent with toluene without complication, and the crystalline nature of the intermediates and final product enables straightforward purification at each stage, including enantiomeric enrichment. 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: 200132-54-3Electric Literature 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. 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.Electric Literature of C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Preparation of O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide as a phase transfer catalyst for the enantioselective alkylation of glycine benzophenone imine tert-butyl ester: (4S)-2-(benzhydrylidenamino)pentanedioic acid, 1-tert-butyl ester-5-methyl ester was written by Corey, E. J.;Noe, Mark C.. And the article was included in Organic Syntheses in 2003.Recommanded Product: (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 preparation of O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (I路Br^–), as a phase transfer catalyst for the enantioselective alkylation of glycine benzophenone imine tert-Bu ester, is reported. 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: 200132-54-3Recommanded Product: (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. Quinuclidine exists in a number of naturally occurring compounds, biologically active agents, and privileged catalysts and ligands for asymmetric catalysis. Quinuclidine is an organic compound and a bicyclic amine and used as a catalyst and a chemical building block. It is a strong base with pKa of the conjugate acid of 19.5. It can be prepared by reduction of quinuclidone.Recommanded Product: (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

Polymeric pseudo-liquid membranes from poly(dodecyl methacrylate): KCl transport and optical resolution was written by Murai, Yuya;Yoshikawa, Masakazu. And the article was included in Polymer Journal (Tokyo, Japan) in 2013.Product Details of 200132-54-3 This article mentions the following:

A polymeric pseudo-liquid membrane (PPLM) was constructed from poly(dodecyl methacrylate) (PC12MA), which exhibited a rubbery state under membrane transport conditions and was used as the membrane matrix, and from dibenzo-18-crown-6 (DB18C6) or O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (AAMC), which was used as a model transporter. Membrane performance was studied using KCl or a racemic mixture of phenylglycine (Phegly) as a model substrate. The PPLM with DB18C6 transported KCl. The membrane transport ability depended on the DB18C6 concentration, implying that DB18C6 worked as a transporter within the PC12MA membrane matrix. L-Phegly was preferentially transported over D-Phegly through the membrane with AAMC from the racemic mixture of Phegly, and the permselectivity was determined to be 1.55. The present results suggest that PPLMs are applicable not only in metal ion transport but also in optical resolution 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 acts as a catalyst, a chemical building block and is used in organic synthesis. It is employed to prepare quinine and alkaloids. Quinuclidine is an organic compound and a bicyclic amine and used as a catalyst and a chemical building block. It is a strong base with pKa of the conjugate acid of 19.5. It can be prepared by reduction of quinuclidone.Product Details of 200132-54-3

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Synthesis of 4-Fluoro-尾-(4-fluorophenyl)-L-phenylalanine by an Asymmetric Phase-Transfer Catalyzed Alkylation: Synthesis on Scale and Catalyst Stability was written by Patterson, Daniel E.;Xie, Shiping;Jones, Lynda A.;Osterhout, Martin H.;Henry, Christopher G.;Roper, Thomas D.. And the article was included in Organic Process Research & Development in 2007.Recommanded Product: (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:

4-Fluoro-尾-(4-fluorophenyl)-L-phenylalanine hydrochloride salt was synthesized by the asym. alkylation of tert-Bu glycinate-benzophenone Schiff base using a cinchona alkaloid as a chiral phase transfer catalyst. Upon scaling, it was observed that to achieve high levels of enantioselectivity, it was necessary to add the catalyst or base last. From these studies, insight into the stability of the catalyst under the reaction conditions was gained. 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: 200132-54-3Recommanded Product: (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 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. Processes involving the fragmentation of quinuclidines in chemical reactions and under electron impact and reactions involving expansion of the quinuclidine ring and intermediate cleavage of the bicyclic system are examined.聽 Quinuclidine is an organic compound and a bicyclic amine and used as a catalyst and a chemical building block. It is a strong base with pKa of the conjugate acid of 19.5. It can be prepared by reduction of quinuclidone.Recommanded Product: (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

Stereocontrolled [¹¹C]alkylation of N-terminal glycine Schiff bases to obtain dipeptides was written by Filp, Ulrike;Pekosak, Aleksandra;Poot, Alex J.;Windhorst, Albert D.. And the article was included in European Journal of Organic Chemistry in 2017.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 use of various quaternary ammonium salts as chiral phase-transfer catalysts allowed effective and stereoselective radiochem. [¹¹C]alkylation to obtain functionalized dipeptides. We herein report a broadly applicable procedure for the asym. [¹¹C]alkylation of dipeptides to give labeled N-terminal peptides by using different [¹¹C]alkyl halides. Contended stereoselectivities of the reactions were observed by using ¹¹C-labeled alkyl halides, [¹¹C]methyl iodide and [¹¹C]benzyl iodide, and diastereomeric ratios with different specialized catalysts of 95:5 and 90:10 were achieved, resp. Accordingly, the straightforward synthesis of enantioenriched compounds should play a vital role in peptide-based radiopharmaceutical development and positron emission tomog. imaging. 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. 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. Quinuclidine is an organic compound and a bicyclic amine and used as a catalyst and a chemical building block. It is a strong base with pKa of the conjugate acid of 19.5. It can be prepared by reduction of quinuclidone.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

Polymeric pseudo-liquid membranes from poly(N-oleylacrylamide) was written by Shiono, Hiroko;Yoshikawa, Masakazu. And the article was included in Membranes (Basel, Switzerland) in 2014.Computed Properties of C37H37BrN2O This article mentions the following:

A polymeric pseudo-liquid membrane (PPLM) was constructed from poly(N-oleylacrylamide) (PC18AAm), which exhibited a rubbery state under membrane transport conditions and used as the membrane matrix. In the present study, dibenzo-18-crown-6 (DB18C6) and dibenzo-21-crown-7 (DB21C7) were adopted as transporters for alkali metal ions. KCl was adopted as a model substrate for DB18C6 and CsCl the latter. Chiral transporter, O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (AAMC) was used as a transporter for chiral separation of a racemic mixture of phenylglycine (Phegly). The L-somer was transported in preference to the antipode. The present study revealed that PPLMs are applicable to membrane transport, such as metal ion transport and 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: 200132-54-3Computed 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. Traditionally, quinuclidine scaffolds can be constructed by second-order nucleophilic substitution (SN2) reaction or condensation reaction of piperidine derivatives. However, most of these reactions are racemic or chiral auxiliary-assisted processes.Computed Properties of C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider

Palladium-catalyzed asymmetric allylic alkylation in the presence of chiral cinchonidinium salts was written by Mang, Joo Yang;Whang, Il Sun;Kwon, Dae Gil;Kim, Dae Young. And the article was included in Journal of the Korean Chemical Society in 2008.Application In Synthesis 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:

Pd-catalyzed enantioselective allylic alkylation of malonates R¹O₂CCH(R²)CO₂R¹ (R¹ = Me, Et, Bn; R² = Me) with rac-1,3-diphenyl-2-propenyl acetate in the presence of cinchona alkaloids gave compounds I in moderate yields and selectivities. 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 In Synthesis 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. 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.Application In Synthesis 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

Asymmetric Synthesis of 尾-Hydroxy Amino Acids via Aldol Reactions Catalyzed by Chiral Ammonium Salts was written by Mettath, Sashikumar;Srikanth, G. S. C.;Dangerfield, Benjamin S.;Castle, Steven L.. And the article was included in Journal of Organic Chemistry in 2004.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 cinchona alkaloid-derived chiral ammonium salt developed by Park and Jew functions as an effective catalyst for the synthesis of 尾-hydroxy 伪-amino carboxylic acids via asym. aldol reactions under homogeneous conditions. The syn diastereomers are obtained in good ee, and aryl-substituted aliphatic aldehydes are the best substrates for the reaction. These results represent the highest ee’s obtained to date in direct aldol reactions of glycine equivalent catalyzed by inexpensive, readily prepared chiral ammonium salts. The (+)-10,11-dihydro-9-(2-propenyloxy)-1-[(2,3,4-trifluorophenyl)methyl]cinchonanium bromide (I) was prepared from dihydrocinchonine, trifluorobenzyl bromide, and allyl bromide. I was evaluated as stereoselective catalyst for the aldol condensation of benzenepropanal with N-(diphenylmethylene)glycine 1,1-dimethylethyl ester. 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. In alkane solvents quinuclidine is a Lewis base that forms adducts with a variety of Lewis acids. Traditionally, quinuclidine scaffolds can be constructed by second-order nucleophilic substitution (SN2) reaction or condensation reaction of piperidine derivatives. However, most of these reactions are racemic or chiral auxiliary-assisted processes.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

Designing Light-Activated Charge-Separating Proteins with a Naphthoquinone Amino Acid was written by Lichtenstein, Bruce R.;Bialas, Chris;Cerda, Jose F.;Fry, Bryan A.;Dutton, P. Leslie;Moser, Christopher C.. And the article was included in Angewandte Chemie, International Edition in 2015.Synthetic Route of C37H37BrN2O This article mentions the following:

The first principles design of manmade redox-protein maquettes is used to clarify the phys./chem. engineering supporting the mechanisms of natural enzymes with a view to recapitulate and surpass natural performance. Herein, we use intein-based protein semisynthesis to pair a synthetic naphthoquinone amino acid (Naq) with histidine-ligated photoactive metal-tetrapyrrole cofactors (i.e., heme and ZnPPIX), creating a 100 渭s photochem. charge separation unit akin to photosynthetic reaction centers. By using propargyl groups to protect the redox-active para-quinone during synthesis and assembly while permitting selective activation, we gain the ability to employ the quinone amino acid redox cofactor with the full set of natural amino acids in protein design. Direct anchoring of quinone to the protein backbone permits secure and adaptable control of intraprotein electron-tunneling distances and rates. 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: 200132-54-3Synthetic Route 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. Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. 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.Synthetic Route of C37H37BrN2O

Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider