Category: 343338-28-3

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

Li, Bowen published the artcileNickel-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Imines, Application In Synthesis of 343338-28-3, the main research area is asym hydrogenation sulfonyl imine nickel catalyst quinoxaline phosphine ligand; amines; asymmetric catalysis; hydrogenation; nickel; reaction mechanisms.

An efficient nickel-catalyzed asym. hydrogenation of N-tert-Bu-sulfonyl imines was developed with excellent yields and enantioselectivities using (R,R)-QuinoxP*, I, as a chiral ligand. The use of a much lower catalyst loading (0.0095 mol %, S/C=10500) represents the highest catalytic activity for the Ni-catalyzed asym. hydrogenations reported so far. Mechanistic studies suggest that a coordination equilibrium exists between the nickel salt and its complex, and that excess nickel salt promotes the formation of the active Ni-complex, and therefore improved the efficiency of the hydrogenation. The catalytic cycle was also investigated by calculations to determine the origin of the enantioselectivity. An extensive network of numerous weak attractive interactions was found to exist between the catalyst and substrate in the transition state and may also contribute to the high catalytic activity.

Angewandte Chemie, International Edition 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

Thakur, Nimisha published the artcileEnantiomeric impurities in chiral catalysts, auxiliaries, and synthons used in enantioselective syntheses. Part 5, COA of Formula: C4H11NOS, the main research area is chiral catalyst synthon enantioselective enantiomeric impurity; chiral separation; enantiomeric excess; enantiomeric impurity; enantioselective syntheses.

The enantiomeric excess of chiral starting materials is one of the important factors determining the enantiopurity of products in asym. synthesis. Fifty-one com. available chiral reagents used as building blocks, catalysts, and auxiliaries in various enantioselective syntheses were assayed for their enantiomeric purity. The test results were classified within five impurities level (ie, <0.01%, 0.01%-0.1%, 0.1%-1%, 1%-10%, >10%). Previously from 1998 to 2013, several reports have been published on the enantiomeric composition of more than 300 chiral reagents. This series of papers is necessitated by the fact that new reagents are forthcoming and that the enantiomeric purity of the same reagent can vary from batch to batch and/or from supplier to supplier. This report presents chiral liquid chromatog. (LC) and gas composition(GC) methods to sep. enantiomers of chiral compounds and evaluate their enantiomeric purities. The accurate and efficient LC anal. was done using newly introduced superficially porous particle (SPP 2.7μm) based chiral stationary phases (TeicoShell, VancoShell, LarihcShell-P, and NicoShell).

Chirality 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, COA of Formula: C4H11NOS.

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

Wilding, Birgit published the artcileInvestigating the phosphinic acid tripeptide mimetic DG013A as a tool compound inhibitor of the M1-aminopeptidase ERAP1, Quality Control of 343338-28-3, the main research area is phosphinic acid tripeptide mimetic enantioselective synthesis inhibitor aminopeptidase ERAP1; peptidomimetic phosphinic acid library synthesis tool probe; chirality condensation protection phospha Michael addition epimerization resolution; enzyme inhibitor structure activity drug discovery target permeability; ERAP1 DG013A bound crystal structure mol docking antitumor agent; Chemical probe; DG013A; ERAP1; M1-aminopeptidase; Permeability.

ERAP1 is a zinc-dependent M1-aminopeptidase that trims lipophilic amino acids from the N-terminus of peptides. Owing to its importance in the processing of antigens and regulation of the adaptive immune response, dysregulation of the highly polymorphic ERAP1 has been implicated in autoimmune disease and cancer. To test this hypothesis and establish the role of ERAP1 in these disease areas, high affinity, cell permeable and selective chem. probes are essential. DG013A 1, is a phosphinic acid tripeptide mimetic inhibitor with reported low nanomolar affinity for ERAP1. However, this chemotype is a privileged structure for binding to various metal-dependent peptidases and contains a highly charged phosphinic acid moiety, so it was unclear whether it would display the high selectivity and passive permeability required for a chem. probe. Therefore, we designed a new stereoselective route to synthesize a library of DG013A 1 analogs to determine the suitability of this compound as a cellular chem. probe to validate ERAP1 as a drug discovery target.

Bioorganic & Medicinal Chemistry Letters published new progress about (Benzyloxy)carbonyl group. 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