Heterocyclic Building Blocks-Tetrahydropyran

Synthetic Route of C5H9BrOIn 2019 ,《Discovery of novel, potent, isosteviol-based antithrombotic agents》 appeared in European Journal of Medicinal Chemistry. The author of the article were Chen, Peng; Zhang, Dianwen; Li, Meng; Wu, Qiong; Lam, Yuko P. Y.; Guo, Yan; Chen, Chen; Bai, Nan; Malhotra, Shipra; Li, Wei; O’Connor, Peter B.; Fu, Hongzheng. The article conveys some information:

Thrombosis is a pathol. coagulation process and can lead to many serious thrombotic diseases. Here, we report a novel potent antithrombotic compound (6k) based on isosteviol with anticoagulant and antiplatelet activities. 6k selectively inhibited FXa (Ki = 0.015μM) against a panel of serine proteases and showed excellent anticoagulant activity (significant prolongation of ex vivo PT and aPTT over the vehicle, p < 0.01). 6k also significantly inhibited ADP-induced platelet aggregation in rats relative to the vehicle (p < 0.01). Furthermore, 6k exhibited potent ex vivo and in vivo antithrombotic activity in rats relative to the vehicle (p < 0.01 and p < 0.0001, resp.). Novel structure 6k, with potent antithrombotic activity, is expected to lead a promising approach for the development of antithrombotic agents. The experimental part of the paper was very detailed, including the reaction process of 4-Bromotetrahydropyran(cas: 25637-16-5Synthetic Route of C5H9BrO)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Synthetic Route of C5H9BrO

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Related Products of 25637-16-5In 2018 ,《Arene-Ligand-Free Ruthenium(II/III) Manifold for meta-C-H Alkylation: Remote Purine Diversification》 was published in Chemistry – A European Journal. The article was written by Fumagalli, Fernando; Warratz, Svenja; Zhang, Shou-Kun; Rogge, Torben; Zhu, Cuiju; Stueckl, A. Claudia; Ackermann, Lutz. The article contains the following contents:

Meta-Selective C-H alkylations of bioactive purine derivatives were accomplished by versatile ruthenium catalysis. Thus, the arene-ligand-free complex [Ru(OAc)2(PPh3)2] enabled remote C-H functionalizations with ample scope and excellent levels of chemo- and positional selectivities. Detailed exptl. and computational mechanistic studies provided strong support for a facile C-H activation within a ruthenium(II/III) manifold. In the experiment, the researchers used 4-Bromotetrahydropyran(cas: 25637-16-5Related Products of 25637-16-5)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Related Products of 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

《Electroreductive Carbofunctionalization of Alkenes with Alkyl Bromides via a Radical-Polar Crossover Mechanism》 was written by Zhang, Wen; Lin, Song. Recommanded Product: 25637-16-5 And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

Electrochem. grants direct access to reactive intermediates (radicals and ions) in a controlled fashion toward selective organic transformations. This feature has been demonstrated in a variety of alkene functionalization reactions, most of which proceed via an anodic oxidation pathway. In this report, we further expand the scope of electrochem. to the reductive functionalization of alkenes. In particular, the strategic choice of reagents and reaction conditions enabled a radical-polar crossover pathway wherein two distinct electrophiles can be added across an alkene in a highly chemo- and regioselective fashion. Specifically, we used this strategy in the intermol. carboformylation, anti-Markovnikov hydroalkylation, and carbocarboxylation of alkenes – reactions with rare precedents in the literature – by means of the electroreductive generation of alkyl radical and carbanion intermediates. These reactions employ readily available starting materials (alkyl halides, alkenes, etc.) and simple, transition-metal-free conditions and display broad substrate scope and good tolerance of functional groups. A uniform protocol can be used to achieve all three transformations by simply altering the reaction medium. This development provides a new avenue for constructing Csp3-Csp3 bonds. In addition to this study using 4-Bromotetrahydropyran, there are many other studies that have used 4-Bromotetrahydropyran(cas: 25637-16-5Recommanded Product: 25637-16-5) was used in this study.

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Recommanded Product: 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

The author of 《Fe-Catalyzed Reductive Couplings of Terminal (Hetero)Aryl Alkenes and Alkyl Halides under Aqueous Micellar Conditions》 were Pang, Haobo; Wang, Ye; Gallou, Fabrice; Lipshutz, Bruce H.. And the article was published in Journal of the American Chemical Society in 2019. HPLC of Formula: 25637-16-5 The author mentioned the following in the article:

The combination of a vinyl-substituted aromatic or heteroaromatic and an alkyl bromide or iodide leads, in the presence of Zn and a catalytic amount of an Fe(II) salt, to a net reductive coupling. The new C-C bond is regiospecifically formed at rt at the β-site of the alkene. The coupling only occurs in an aqueous micellar medium, where a radical process is likely, supported by several control experiments A mechanism based on these data is proposed. In the experimental materials used by the author, we found 4-Bromotetrahydropyran(cas: 25637-16-5HPLC of Formula: 25637-16-5)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.HPLC of Formula: 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

He, Rong-De; Bai, Yunfei; Han, Guan-Yu; Zhao, Zhen-Zhen; Pang, Xiaobo; Pan, Xiaobo; Liu, Xue-Yuan; Shu, Xing-Zhong published an article in 2022. The article was titled 《Reductive Alkylation of Alkenyl Acetates with Alkyl Bromides by Nickel Catalysis》, and you may find the article in Angewandte Chemie, International Edition.Application In Synthesis of 4-Bromotetrahydropyran The information in the text is summarized as follows:

Herein a cross-electrophile reaction of alkenyl acetates with alkyl bromides was reported. This work has enabled a new method for the synthesis of aliphatic alkenes from alkenyl acetates to be established that was used to add more structural complexity and mol. diversity with enhanced functionality tolerance. The method allows for a gram-scale reaction and modification of biol. active mols., and it affords access to useful building blocks. Preliminary mechanistic studies revealed that the Ni(I) species plays an essential role for the success of the coupling of these two reactivity-mismatched electrophiles. In the experimental materials used by the author, we found 4-Bromotetrahydropyran(cas: 25637-16-5Application In Synthesis of 4-Bromotetrahydropyran)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Application In Synthesis of 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

《Expanding the Medicinal Chemist Toolbox: Comparing Seven C(sp2)-C(sp3) Cross-Coupling Methods by Library Synthesis》 was published in ACS Medicinal Chemistry Letters in 2020. These research results belong to Dombrowski, Amanda W.; Gesmundo, Nathan J.; Aguirre, Ana L.; Sarris, Katerina A.; Young, Jonathon M.; Bogdan, Andrew R.; Martin, M. Cynthia; Gedeon, Shasline; Wang, Ying. Name: 4-Bromotetrahydropyran The article mentions the following:

Despite recent advances in the field of C(sp2)-C(sp3) cross-couplings and the accompanying increase in publications, it can be hard to determine which method is appropriate for a given reaction when using the highly functionalized intermediates prevalent in medicinal chem. Thus a study was done comparing the ability of seven methods to directly install a diverse set of alkyl groups on “”drug-like”” aryl structures via parallel library synthesis. Each method showed substrates that it excelled at coupling compared with the other methods. When analyzing the reactions run across all of the methods, a reaction success rate of 50% was achieved. Whereas this is promising, there are still gaps in the scope of direct C(sp2)-C(sp3) coupling methods, like tertiary group installation. The results reported herein should be used to inform future syntheses, assess reaction scope, and encourage medicinal chemists to expand their synthetic toolbox. The results came from multiple reactions, including the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Name: 4-Bromotetrahydropyran)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Name: 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Duvadie, Rohit; Pomberger, Alexander; Mo, Yiming; Altinoglu, Erhan I.; Hsieh, Hsiao-Wu; Nandiwale, Kakasaheb Y.; Schultz, Victor L.; Jensen, Klavs F.; Robinson, Richard I. published an article in 2021. The article was titled 《Photoredox Iridium-Nickel Dual Catalyzed Cross-Electrophile Coupling: From a Batch to a Continuous Stirred-Tank Reactor via an Automated Segmented Flow Reactor》, and you may find the article in Organic Process Research & Development.Product Details of 25637-16-5 The information in the text is summarized as follows:

Organic reaction optimization for batch to flow transfer represents a main challenge for process chemists in drug synthesis. Several factors such as reactant concentration, residence/reaction time, or homo-/heterogeneity need to be taken into consideration during the fine-tuning of reaction conditions toward typical scale-up goals, such as high space-time yield. Herein, we present reaction optimization for photoredox iridium-nickel dual catalyzed cross-electrophile coupling with a focus on developing homogeneous starting conditions. During the screening, special attention was put on the replacement of inorganic bases with homogeneous organic bases, and the effect of pKa on the reaction yield was investigated. Screening was conducted via an automated segmented flow reactor at 15μL scale, and subsequentially, the conditions were transferred to a 5 mL photo-continuous stirred-tank reactor (CSTR) cascade to demonstrate multigram continuous flow synthesis during a 24 h steady operation. In addition to this study using 4-Bromotetrahydropyran, there are many other studies that have used 4-Bromotetrahydropyran(cas: 25637-16-5Product Details of 25637-16-5) was used in this study.

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Product Details of 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

In 2022,Romano, Ciro; Talavera, Laura; Gomez-Bengoa, Enrique; Martin, Ruben published an article in Journal of the American Chemical Society. The title of the article was 《Conformational Flexibility as a Tool for Enabling Site-Selective Functionalization of Unactivated sp3 C-O Bonds in Cyclic Acetals》.Formula: C5H9BrO The author mentioned the following in the article:

A dual catalytic manifold that enables site-selective functionalization of unactivated sp3 C-O bonds in cyclic acetals with aryl and alkyl halides is reported. The reaction is triggered by an appropriate σ*-p orbital overlap prior to sp3 C-O cleavage, thus highlighting the importance of conformational flexibility in both reactivity and site selectivity. The protocol is characterized by its excellent chemoselectivity profile, thus offering new vistas for activating strong σ sp3 C-O linkages. In addition to this study using 4-Bromotetrahydropyran, there are many other studies that have used 4-Bromotetrahydropyran(cas: 25637-16-5Formula: C5H9BrO) was used in this study.

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Formula: C5H9BrO

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Application In Synthesis of 4-BromotetrahydropyranIn 2018 ,《Bench-Stable Stock Solutions of Silicon Grignard Reagents: Application to Iron- and Cobalt-Catalyzed Radical C(sp3)-Si Cross-Coupling Reactions》 was published in Angewandte Chemie, International Edition. The article was written by Xue, Weichao; Shishido, Ryosuke; Oestreich, Martin. The article contains the following contents:

A robust method for the preparation of silicon-based magnesium reagents is reported. The MgBr2 used in the lithium-to-magnesium transmetalation step is generated in situ from 1,2-dibromoethane and elemental magnesium in hot THF. No precipitation of MgBr2 occurs in the heat, and transmetalation at elevated temperature leads to homogeneous stock solutions of the silicon Grignard reagents that are stable and storable in the fridge. This method avoids the preparation of silicon pronucleophiles such as Si-Si and Si-B reagents. The new Grignard reagents were applied to unprecedented iron- and cobalt-catalyzed cross-coupling reactions of unactivated alkyl bromides. The functional-group tolerance of these magnesium reagents is excellent. In the experiment, the researchers used many compounds, for example, 4-Bromotetrahydropyran(cas: 25637-16-5Application In Synthesis of 4-Bromotetrahydropyran)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Application In Synthesis of 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

In 2017,Zhou, Wen-Jun; Cao, Guang-Mei; Shen, Guo; Zhu, Xing-Yong; Gui, Yong-Yuan; Ye, Jian-Heng; Sun, Liang; Liao, Li-Li; Li, Jing; Yu, Da-Gang published 《Visible-Light-Driven Palladium-Catalyzed Radical Alkylation of C-H Bonds with Unactivated Alkyl Bromides》.Angewandte Chemie, International Edition published the findings.Safety of 4-Bromotetrahydropyran The information in the text is summarized as follows:

Reported herein is a novel visible-light photoredox system with Pd(PPh3)4 as the sole catalyst for the realization of the first direct cross-coupling of C(sp3)-H bonds in N-aryl tetrahydroisoquinolines with unactivated alkyl bromides. Moreover, intra- and intermol. alkylations of heteroarenes were also developed under mild reaction conditions. A variety of tertiary, secondary and primary alkyl bromides undergo reaction to generate C(sp3)-C(sp3) and C(sp2)-C(sp3) bonds in moderate to excellent yields. These redox-neutral reactions feature broad substrate scope (>60 examples), good functional-group tolerance and facile generation of quaternary centers. Mechanistic studies indicate that the simple palladium complex acts as the visible-light photocatalyst and radicals are involved in the process. The experimental part of the paper was very detailed, including the reaction process of 4-Bromotetrahydropyran(cas: 25637-16-5Safety of 4-Bromotetrahydropyran)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Safety of 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics