Category: 343338-28-3

Zhou, Li published the artcileSelective Synthesis of Single-Handed Helical Polymers from Achiral Monomer and a Mechanism Study on Helix-Sense-Selective Polymerization, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide, the main research area is helicity conformation single handed polyphenyl isocyanide preparation; chiral polymers; helix; helix-sense-selective polymerization; living polymerization; polymers.

Inspired by the exquisite helixes in nature, fabrication of helical materials with controlled handedness has attracted considerable attention. Herein, the authors report on precise synthesis of single left- and right-handed helical polyisocyanides through living polymerization of achiral monomers using chiral palladium catalysts under helix-sense-selective manner. Mechanism study revealed that the yielded helixes with opposite handedness showed different activity of the living chain end. The helix with unfavored handedness was self-terminated, while the one with favored handedness showed high activity and could undergo chain propagation to form a high mol. weight polymer with maintained single-handed helicity.

Angewandte Chemie, International Edition published new progress about Helicity. 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

Zhang, Shu-Wei published the artcileSynthesis and in Vitro and in Vivo Biological Evaluation of Tissue-Specific Bisthiazole Histone Deacetylase (HDAC) Inhibitors, Product Details of C4H11NOS, the main research area is bisthiazole derivative preparation anticancer HDAC inhibitor.

A series of bisthiazole-based hydroxamic acids as novel potent HDAC inhibitors was developed during our previous work. In the present work, a new series of highly potent bisthiazole-based compounds were designed and synthesized. Among the prepared compounds, compound I, which contains an α-(S)-methyl-substituted benzyl group, displays potent inhibitory activity toward human HDACs and several cancer cells lines. Compound I has a favorable PK profile and high tissue distribution specificity in the colon, as well as good efficacy in the AOM-DSS mouse model for colitis-associated colonic tumorigenesis.

Journal of Medicinal Chemistry published new progress about Amidation. 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

Kawada, Takuma published the artcileAsymmetric Transfer Hydrogenative Amination of Benzylic Ketones Catalyzed by Cp*Ir(III) Complexes Bearing a Chiral N-(2-Picolyl)sulfonamidato Ligand, Category: amides-buliding-blocks, the main research area is amine preparation chemoselective diastereoselective enantioselective; benzylic ketone asym transfer hydrogenative amination iridium complex catalyst.

A convenient asym. reductive amination of benzylic ketones (α-arylated ketones) catalyzed by newly designed Cp*Ir complexes bearing a chiral N-(2-picolyl)sulfonamidato ligand was developed. Using readily available β-amino alcs. as chiral aminating agents, a range of benzo-fused and acyclic ketones were successfully reduced with formic acid in methanol at 40°C to afford amines with favorable chemo- and diastereoselectivities. The amino alc.-derived chiral auxiliary was easily removed by mild periodic oxidants, leading to optically active primary β-arylamines without erosion of the optical purity (up to 97% ee). The excellent catalytic performance was retained even upon lowering the amount of catalyst to a substrate/catalyst (S/C) ratio of 20,000, and the amination could be performed on a large scale exceeding 100 g. The precise hydride transfer to iminium species generated from the ketonic substrate and the chiral amine counterpart was suggested by the mechanistic studies on stoichiometric reactions of isolable hydridoiridium complexes and model intermediates such as N,O-acetal, enamine, and iminium compounds

Journal of Organic Chemistry published new progress about Amination. 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

Li, Chun-Tian published the artcileRearrangement of N-tert-Butanesulfinyl Enamines for Synthesis of Enantioenriched α-Hydroxy Ketone Derivatives, Formula: C4H11NOS, the main research area is acyclic tertiary hydroxy sulfenyloxy ketone preparation enantioselective; tert butanesulfinyl ketimine methyl triflate cascade enamination methylation rearrangement.

Treating chiral N-tert-butanesulfinyl ketimines with potassium hexamethyldisilazide (or potassium tert-butoxide) and Me triflate gives N-methylated N-tert-butanesulfinyl enamine intermediates that undergo stereoselective [2,3]-rearrangement to afford α-sulfenyloxy ketones I (R = Ph, iPr, 2-furyl, etc.; R’ = Me, allyl, Bn, etc.) with excellent enantiopurities. This cascade of enamination-N-methylation-rearrangement was even used to generate acyclic tertiary α-hydroxy ketones, II bearing two α-substituents showing negligible differences in bulkiness, such as Me and Et groups.

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

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

Kamimura, Akio published the artcileA study on the stereochemistry of direct conversion of polyamides to hydroxyesters using monomeric secondary chiral amines as a model compound, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide, the main research area is stereochem mechanism polyamide hydroxyester secondary chiral amine model compound.

Stereochem. of direct conversion of polyamides to hydroxyesters was investigated using model compounds Optically active secondary-alkyl amines underwent the conversion to corresponding secondary alcs. in moderate yields by treatment with supercritical methanol in the presence of glycolic acid. The reaction progressed through almost completely stereochem. inversion to give secondary alcs. in high yields. The substitution reaction of amino group to hydroxyl group progressed through SN2 transition state accompanying with stereoinversion.

Polymer Degradation and Stability published new progress about Chirality. 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

Zhang, Yaqi published the artcileEnantioselective Syntheses of Axially Chiral Phosphonates or Phosphine Oxides via Asymmetric Suzuki Reactions with Chiral Sulfinamide Monophosphine Ligands, Synthetic Route of 343338-28-3, the main research area is stereoselective Suzuki chiral sulfinamide phosphine oxide phosphonate chiral preparation.

A class of chiral sulfinamide monophosphine ligands Ming-Phos were firstly employed in the asym. Suzuki coupling reactions. Using the in-situ formed catalyst from PdCl2 and (R, SS)-M07, 22 axially chiral phosphonates or phosphine oxides were successfully synthesized in 29-99% yields with up to 98% ee. This method provides a simple and efficient protocol for the synthesis of axially chiral biaryl monophosphine oxides.

ChemistrySelect published new progress about Chirality. 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

Nimje, Roshan Y. published the artcileDevelopment of a Stereoselective and Scalable Synthesis for the Potent Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitor, BMT-297376; N-((R)-1-((cis)-4-(3-(Difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl)propyl)-6-methoxynicotinamide, Quality Control of 343338-28-3, the main research area is difluoromethyl methoxypyridinyl cyclohexyl methoxynicotinamide preparation enantioselective indoleamine dioxygenase inhibitor.

The current work describes a stereoselective and scalable route to N-((R)-1-((cis)-4-(3-(difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl)propyl)-6-methoxynicotinamide I from readily available 1,4-dioxaspiro[4.5]decan-8-one. The developed process encompasses an efficient 1,4-trans-selective synthesis of (trans)-4-(3-(difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl methanesulfonate as the key intermediate and the use of Ellman sulfinamine methodol. to install an alkyl amine in a stereoselective manner. Various synthetic routes were screened to accomplish a stereoselective and scalable protocol to access the title compound I. This advancement enabled a competent route to the title compound in an enantioselective, safe, cost-effective, and scalable manner.

Organic Process Research & Development published new progress about Cyanation. 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

Zheng, Bin published the artcileStereoselective synthesis of a tubulysin core for antibody-drug conjugate studies, Computed Properties of 343338-28-3, the main research area is tripeptide enantioselective synthesis tubulysin core antibody drug conjugate; peptide coupling amidation hydrosilation sulfinimine steric effect.

An expeditious synthesis of an advanced tripeptide intermediate en route to a tubulysin antibody-drug conjugate payload is described. The efficient formation of an N-Pr tertiary amide required tailoring the amine component to reduce steric demand. Addnl., double activation of the carboxylate was required via an aluminum-Lewis acid coupled activated ester strategy to enable the formation of the highly congested amide bond with superior retention of stereochem. integrity. Other permutations of reactant structure and reagents met with failure. The realization of this key direct bond construction enabled a convergent solution-phase synthesis of the unnatural tubulysin tripeptide in a highly convergent manner from three simple building blocks in eight steps and 22.4% overall yield utilizing only a single silica gel chromatog. purification

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

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

Goswami, Prithwish published the artcileEfficient access to general α-tertiary amines via water-accelerated organocatalytic multicomponent allylation, Quality Control of 343338-28-3, the main research area is tertiary amine preparation; ketone allyl boronic acid ester benzhydrazide multicomponent allylation organocatalyst; ketoester allyl boronic acid ester benzhydrazide multicomponent allylation organocatalyst; allyl boronic acid ester ketoester amine multicomponent allylation organocatalyst.

A tetrasubstituted carbon atom connected by three sp3 or sp2-carbons with single nitrogen, i.e., the α-tertiary amines I [R = n-Pr, CH2CO2Et, Ph, etc.; R1 = Me, Et, n-Pr, etc.], was an essential structure of diverse naturally occurring alkaloids and pharmaceuticals. The synthetic approach toward ATA structures was intricate, therefore, a straightforward catalytic method had remained a substantial challenge. Herein, an efficient water-accelerated organocatalytic allylation to directly access ATA incorporating homoallylic amine structures I by exploiting readily accessible general ketones/keto esters as useful starting material along with allyl boronic acid esters and benzhydrazide/amines. The synergistic action of a hydrophobic Bronsted acid in combination with a squaramide hydrogen-bonding donor under aqueous condition enabled the facile formation of the desired moiety I. The developed exceptionally mild but powerful system facilitated a broad substrate scope and enabled efficient multi-gram scalability.

Nature Communications published new progress about Allylation. 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

McKerrall, Steven J. published the artcileStructure- and Ligand-Based Discovery of Chromane Arylsulfonamide Nav1.7 Inhibitors for the Treatment of Chronic Pain, Quality Control of 343338-28-3, the main research area is pain analgesic chromane arylsulfonamide sodium channel crystal structure pharmacokinetics.

Using structure- and ligand-based design principles, a novel series of piperidyl chromane arylsulfonamide Nav1.7 inhibitors was discovered. Early optimization focused on improvement of potency through refinement of the low energy ligand conformation and mitigation of high in vivo clearance. An in vitro hepatotoxicity hazard was identified and resolved through optimization of lipophilicity and LLE to arrive at GNE-616 (24(I)), a highly potent, metabolically stable, subtype selective inhibitor of Nav1.7. I showed a robust PK/PD response in a Nav1.7 dependent mouse model and site-directed mutagenesis was used to identify residues critical for the isoform selectivity profile of I.

Journal of Medicinal Chemistry published new progress about Analgesics. 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