Tag: M.W=100-150

Shan, Chao published the artcileRapid Synthesis of α-Chiral Piperidines via a Highly Diastereoselective Continuous Flow Protocol, Quality Control of 343338-28-3, the main research area is chiral piperidine preparation diastereoselective; butylsulfinyl imine Grignard reagent debromocyclization continuous flow.

A practical continuous flow protocol has been developed using readily accessible N-(tert-butylsulfinyl)-bromoimine and Grignard reagents, providing various functionalized piperidines (34 examples) in superior results (typically >80% yield and with >90:10 dr) within minutes. The high-performance scale-up is smoothly carried out, and efficient synthesis of the drug precursor further showcases its utility. This flow process offers rapid and scalable access to enantioenriched α-substituted piperidines.

Organic Letters published new progress about Cyclization (debromo-). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Quality Control of 343338-28-3.

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

McDaniel, Jade published the artcileDiscovery of annulating reagents enabling the one-step and highly stereoselective synthesis of cyclopentyl and cyclohexyl cores, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide, the main research area is carbocycle stereoselective preparation tertbutylsulfinyl chlorobutanimidate bromopentanimidate Michael acceptor cycloaddition.

The use of the unprecedented annulating reagents Me N-(tert-butylsulfinyl)-4-chlorobutanimidate and Me N-(tert-butylsulfinyl)-5-bromopentanimidate enables the diastereoselective preparation of 5- and 6-membered carbocycles bearing three contiguous stereocenters. These synthons undergo cycloaddition with a variety of Michael acceptors to form cyclopentane/cyclohexane rings with excellent stereochem. control, generating only one of the eight possible diastereomers. This novel methodol. has enabled the highly enantioselective and high yielding synthesis of novel chemotypes of pharmacol. relevance.

Organic Letters published new progress about Cycloaddition reaction. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide.

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

Raubo, Piotr published the artcileThe discovery and evaluation of 3-amino-2(1H)-pyrazinones as a novel series of selective p38α MAP kinase inhibitors, Application of (S)-2-Methylpropane-2-sulfinamide, the main research area is amino pyrazinone derivative preparation p38MAP kinase inhibitor inhalation structure; AZD6703; AZD7624; COPD; Inflammation; Kinases; P38α.

The discovery and optimization of a novel series of potent and selective p38α inhibitors is described. Evaluating the structure-activity relationship of an aminoalkyl substituent at the 3 position of the 2(1H)-pyrazinone core, p38α potency was increased 20000-fold. The most advanced compound (25) demonstrated excellent in vivo properties suitable for an inhaled route of administration.

Bioorganic & Medicinal Chemistry Letters published new progress about Anti-inflammatory agents. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Application of (S)-2-Methylpropane-2-sulfinamide.

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

Lin, You-Chen published the artcileConcise Synthesis and Antimicrobial Evaluation of the Guanidinium Alkaloid Batzelladine D: Development of a Stereodivergent Strategy, Name: (S)-2-Methylpropane-2-sulfinamide, the main research area is stereodivergent synthesis batzelladine D antimicrobial activity.

Herein, we describe a stereodivergent route to (±)-batzelladine D (2), (+)-batzelladine D (2), (-)-batzelladine D (2), and a series of stereochem. analogs and explore their antimicrobial activity for the first time. The concise synthetic approach enables access to the natural products in a sequence of 8-12 steps from readily available building blocks. Highlights of the synthetic strategy include gram-scale preparation of a late stage intermediate, pinpoint stereocontrol around the tricyclic skeleton, and a modular strategy that enables analog generation. A key bicyclic β-lactam intermediate not only serves as the key controlling element for pyrrolidine stereochem. but also serves as a preactivated coupling partner to install the ester side chain. The stereocontrolled synthesis allowed for the investigation of the antimicrobial activity of batzelladine D, demonstrating promising activity that is more potent for non-natural stereoisomers.

Journal of the American Chemical Society published new progress about Acinetobacter baumannii. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Name: (S)-2-Methylpropane-2-sulfinamide.

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

Yisimayili, Nuermaimaiti published the artcileα-Hydroxylation of α,α-Disubstituted N-tert-Butanesulfinyl Ketimines with Molecular Oxygen: Stereoselective Synthesis of α-Tertiary Hydroxyimines, Related Products of amides-buliding-blocks, the main research area is tertiary hydroxyimine preparation diastereoselective; acyclic ketimine hydroxylation.

The α-tertiary hydroxyimines (Rs/Ss,2R)-ROHC(R1)C=NS(O)t-Bu (R = butan-2-yl, cyclohex-3-en-1-yl, 1-phenylpropyl, etc.; R1 = Ph, 2-propenyl, 2-methoxyphenyl, etc.) were stereoselectively synthesized from enantioenriched N-tert-butanesulfinyl ketimines (Rs/Ss,2R)-RCH(R1)C=NS(O)t-Bu using potassium tert-butoxide, mol. oxygen, and tri-Me phosphite. The stereoselective hydroxylation of acyclic ketimines bearing two sterically similar α-substituents was achieved by controlling the geometry of the metalloenamine intermediates and the facial selectivity of hydroxylation. The synthetic utility of the resulting α-tertiary hydroxyimines was demonstrated through the successful diastereoselective synthesis of highly substituted β-amino alcs.

Organic Letters published new progress about Diastereoselective synthesis. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Related Products of amides-buliding-blocks.

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

Quintavalla, Arianna published the artcileDiastereoselective Synthesis of Chiral Oxathiazine 2-Oxide Scaffolds as Sulfinyl Transfer Agents, Synthetic Route of 343338-28-3, the main research area is chiral oxathiazine oxide preparation diastereoselective sulfinyl transfer agent.

An efficient diastereoselective route for the preparation of chiral oxathiazine 2-oxide scaffolds as sulfinyl transfer agents, using tert-butanesulfinamide (tBSA) both as the source of chirality and as the precursor to the required nitrogen electron withdrawing group on the scaffold, was developed. This methodol. allows the introduction of different substituents on the chiral scaffold, using com. available reagents and standard synthetic transformations. The synthesized scaffolds were tested in the preparation of enantioenriched sulfinamides, providing results comparable to the sulfinyl transfer agents so far proposed in the literature, and opening the possibility to further elaborate these scaffolds, with the aim to support them on solid phases so to facilitate their recovery and reuse.

Advanced Synthesis & Catalysis published new progress about Diastereoselective synthesis. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Synthetic Route of 343338-28-3.

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

Zhang, Lei published the artcileTotal Synthesis of (-)-Alstofolinine A through a Furan Oxidation/Rearrangement and Indole Nucleophilic Cyclization Cascade, Safety of (S)-2-Methylpropane-2-sulfinamide, the main research area is alstofolinine A total synthesis furan oxidation aza Achmatowicz rearrangement; oxidation rearrangement nucleophilic cyclization cascade azabicyclononane core preparation; aza-Achmatowicz rearrangement; furan; indole; natural-product synthesis; selective oxidation.

A reaction cascade of aza-Achmatowicz rearrangement followed by indole nucleophilic cyclization was developed to generate the common indole-fused azabicyclo[3.3.1]nonane core of the macroline family of alkaloids. The key to the success of the strategy relies on the careful manipulation of protecting groups and judicious selection of chemoselective furan oxidation conditions. The synthetic utility was further demonstrated on the asym. total synthesis of (-)-alstofolinine A (I). The compounds were evaluated for their antitumor activity using four cancer cell lines. Differential activities were observed, indicating that indole-containing multicyclic structures can exert potential and selective biomedical properties, justifying them as hit compounds worthy of further development.

Angewandte Chemie, International Edition published new progress about Achmatowicz reaction (aza-). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Safety of (S)-2-Methylpropane-2-sulfinamide.

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

Zhang, Ye published the artcileTotal Synthesis of (-)-Alstofolinine A: Selected Furan Oxidation/ Cyclization Cascade, Product Details of C4H11NOS, the main research area is chemoselective oxidation aza Achmatowicz rearrangement cyclization cascade diastereoselective; alstofolinine A total synthesis.

Indole-fused tetracyclic ring systems containing nitrogen atoms are common core skeletons of many indole alkaloids such as sarpagine, macroline, and ajmaline. Efficient and stereoselective construction of these ring systems can promote the development of the corresponding alkaloid syntheses. In this article, we briefly summarize our current progress toward the application of the aza-Achmatowicz reaction and indole nucleophilic addition reaction cascade for the first asym. total synthesis of the macroline-type indole alkaloid (-)-Alstofolinine A. Our synthetic strategy is based on furan oxidation/rearrangement and proceeds from easily accessible materials such as indole and furan derivatives

Synlett published new progress about Achmatowicz reaction (aza-). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Product Details of C4H11NOS.

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

Hardouin, Christophe published the artcileMultikilogram Synthesis of a Potent Dual Bcl-2/Bcl-xL Antagonist. 2. Manufacture of the 1,3-Diamine Moiety and Improvement of the Final Coupling Reaction, Category: amides-buliding-blocks, the main research area is acylsulfonamide diamine telescoped process aza Reformatsky coupling chemoselective amination.

This paper describes the synthesis of kilogram quantities of the sulfonamide moiety I involved in a coupling reaction with acid moiety II to provide batches of drug candidate III for preclin. studies and first-in-human clin. trials. A first approach relying on a chiral separation furnished the desired enantiomer of 1,3-diamine IV, precursor of sulfonamide I. An enantiomeric synthesis of IV using the Ellman’s chiral auxiliary coupled with an aza-Reformatsky reaction to control the stereochem. is also discussed. Coupling conditions of the final step involving EDCI to provide III under a cGMP process are detailed. An alternative approach using N-(1-methanesulfonyl)benzotriazole is also presented.

Organic Process Research & Development published new progress about Amination (chemoselective). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Category: amides-buliding-blocks.

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

De Croos, Philomen published the artcileDevelopment of a Large-Scale Asymmetric Process for tert-Butanesulfinamide, Application In Synthesis of 343338-28-3, the main research area is butanesulfinamide enantioselective preparation.

Process development for a scalable and green synthesis of chiral tert-butanesulfinamide (TBSA) on a multikilogram scale is reported. The process is based on the identification of a chiral sulfinyl transfer agent, benzo[1,3]oxathiozin-2-one, that contains active and differentiated S-N and S-O bonds, allowing the synthesis to proceed under mild reaction conditions. This method is practical and overcomes the disadvantages of earlier methods deploying harsh reaction conditions and hazardous and toxic reagents.

Organic Process Research & Development published new progress about Enantioselective synthesis. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Application In Synthesis of 343338-28-3.

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