Tag: M.W=350-400

Neelam, Uday Kumar published the artcileMetathesis approach to the formal synthesis of aliskiren, SDS of cas: 172900-69-5, the main research area is aliskiren Tekturna Rasilez renin inhibitor antihypertensive preparation enantioselective synthesis.

A formal synthesis of aliskiren by employing Grubbs second generation catalyst in a cross olefin metathesis, iron(III)-catalyzed vinylation and biocatalysis (enzyme catalysis) by using PLE is disclosed. The title compounds thus formed included (αS,γS,δS,ζS)-δ-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-γ-hydroxy-4-methoxy-3-(3-methoxypropoxy)-α,ζ-bis(1-methylethyl)benzeneoctanamide (Aliskiren) (I) and Aliskiren hemifumarate. The synthesis of the target compound was achieved by a convergent synthesis strategy. A reaction of (3S,5S)-5-[(1S,3S)-1-azido-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methylpentyl]dihydro-3-(1-methylethyl)-2(3H)-furanone with 3-amino-2,2-dimethylpropanamide gave an azide precursor for I, i.e., (αS,γS,δS,ζS)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-δ-azido-γ-hydroxy-4-methoxy-3-(3-methoxypropoxy)-α,ζ-bis(1-methylethyl)benzeneoctanamide.

Chemistry & Biology Interface published new progress about Amidation. 172900-69-5 belongs to class bromides-buliding-blocks, name is 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene, and the molecular formula is C17H27BrO3, SDS of cas: 172900-69-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wang, Fan published the artcileAn Improved and Economical Process for the Manufacture of the Key Intermediate of Aliskiren, a New Potent Renin Inhibitor, Computed Properties of 172900-69-5, the main research area is aliskiren intermediate preparation; aminomethoxymethoxypropoxybenzylmethylhexanoic acid preparation; lhexanoic acid aminomethoxymethoxypropoxybenzylmethyl preparation.

An improved, practical, economical and efficient process for the production of (2S,4S)-2-amino-4-(4-methoxy-3-(3-methoxypropoxy)benzyl)-5-methylhexanoic acid, a key intermediate of the new potent renin inhibitor of aliskiren, in a total yield over 30% is described. This process avoids expensive reagents and chromatog. purifications, and is easily scaled up in industry.

Organic Process Research & Development published new progress about aliskiren intermediate preparation; aminomethoxymethoxypropoxybenzylmethylhexanoic acid preparation; lhexanoic acid aminomethoxymethoxypropoxybenzylmethyl preparation. 172900-69-5 belongs to class bromides-buliding-blocks, name is 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene, and the molecular formula is C17H27BrO3, Computed Properties of 172900-69-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Sun, Xiaoli published the artcileDevelopment of SNAP-Tag Fluorogenic Probes for Wash-Free Fluorescence Imaging, Computed Properties of 352351-55-4, the main research area is SNAP tag fluorogenic probe wash free fluorescence imaging.

The ability to specifically attach chem. probes to individual proteins represents a powerful approach to the study and manipulation of protein function in living cells. It provides a simple, robust and versatile approach to the imaging of fusion proteins in a wide range of exptl. settings. However, a potential drawback of detection using chem. probes is the fluorescence background from unreacted or nonspecifically bound probes. In this report the authors present the design and application of novel fluorogenic probes for labeling SNAP-tag fusion proteins in living cells. SNAP-tag is an engineered variant of the human repair protein O6-alkylguanine-DNA alkyltransferase (hAGT) that covalently reacts with benzylguanine derivatives Reporter groups attached to the benzyl moiety become covalently attached to the SNAP tag while the guanine acts as a leaving group. Incorporation of a quencher on the guanine group ensures that the benzylguanine probe becomes highly fluorescent only upon labeling of the SNAP-tag protein. The authors describe the use of intramolecularly quenched probes for wash-free labeling of cell surface-localized epidermal growth factor receptor (EGFR) fused to SNAP-tag and for direct quantification of SNAP-tagged β-tubulin in cell lysates. In addition, the authors have characterized a fast-labeling variant of SNAP-tag, termed SNAPf, which displays up to a tenfold increase in its reactivity towards benzylguanine substrates. The presented data demonstrate that the combination of SNAPf and the fluorogenic substrates greatly reduces the background fluorescence for labeling and imaging applications. This approach enables highly sensitive spatiotemporal investigation of protein dynamics in living cells.

ChemBioChem published new progress about Cell membrane. 352351-55-4 belongs to class bromides-buliding-blocks, name is (9H-Fluoren-9-yl)methyl (2-aminoethyl)carbamate hydrobromide, and the molecular formula is C17H19BrN2O2, Computed Properties of 352351-55-4.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Hollas, Michael A. published the artcileA Bifunctional Spin Label for Ligand Recognition on Surfaces, Related Products of bromides-buliding-blocks, the main research area is bifunctional spin ligand recognition surfaces; EPR spectroscopy; carbohydrates; nanoparticles; sensors; spin labels.

In situ monitoring of biomol. recognition, especially at surfaces, still presents a significant tech. challenge. ESR of biomols. spin-labeled with nitroxides can offer uniquely sensitive and selective insights into these processes, but new spin-labeling strategies are needed. The synthesis and study of a bromoacrylaldehyde spin label (BASL), which features two attachment points with orthogonal reactivity is reported. The first examples of mannose and biotin ligands coupled to aqueous carboxy-functionalized gold nanoparticles through a spin label are presented. EPR spectra were obtained for the spin-labeled ligands both free in solution and attached to nanoparticles. The labels were recognized by the mannose-binding lectin, Con A, and the biotin-binding protein avidin-peroxidase. Binding gave quantifiable changes in the EPR spectra from which binding profiles could be obtained that reflect the strength of binding in each case.

Angewandte Chemie, International Edition published new progress about ESR (electron spin resonance). 352351-55-4 belongs to class bromides-buliding-blocks, name is (9H-Fluoren-9-yl)methyl (2-aminoethyl)carbamate hydrobromide, and the molecular formula is C17H19BrN2O2, Related Products of bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Goeschke, Richard published the artcileThe nonchiral bislactim diethoxy ether as a highly stereo-inducing synthon for sterically hindered, γ-branched α-amino acids: A practical, large-scale route to an intermediate of the novel renin inhibitor aliskiren, Safety of 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene, the main research area is gamma branched amino acid aliskiren intermediate preparation; stereoslective alkylation gamma branched amino acid preparation.

The diastereoselective synthesis of the sterically hindered, γ-branched α-amino acid derivative, I (R = CO2CMe3), and its N-[(tert-butoxy)carbonyl](Boc)-protected alc., both key intermediates of a novel class of nonpeptide renin inhibitors such as aliskiren, is described. Initially, the analogous Me ester was obtained by alkylation of the chiral Schoellkopf dihydropyrazine with a dialkoxy-substituted alkyl bromide, which proceeded with explicitly high diastereofacial selectivity (ds ≥98%) to give II, followed by mild acid hydrolysis and N-Boc protection. Conversely, the complete lack of stereocontrol and poor yields suggested, in addition to the anticipated shielding effect by the iPr group at C(2) of the auxiliary, steric repulsion between the MeO-C(6) and bulky residues in the proposed transition state, which would strongly disfavor both the Si and Re attack of the electrophile. Based on this rationale, alkylation of a readily accessible achiral diethoxy-dihydropyrazine was found to provide a 95:5 mixture of the product diastereoisomers in high yield, which afforded in two steps and after recrystallization enantiomerically pure I (R = CO2CMe3). Similarly, the stereochem. course for the alkylation reactions of the related alkyl bromides was investigated. The precursor bromides were efficiently synthesized via the diastereoselective alkylation of the Evans 3-isovaleroyloxazolidin-2-ones either with a bromide or with benzyl chloromethyl ether, and subsequent standard transformations. A practical and economical protocol of the preparation of I (R = CO2CMe3) on a multi-100-g scale is given. This is the first report of the application of an achiral dihydropyrazine, as a highly stereo-inducing synthon providing rapid access to a N-protected γ-branched α-amino acid with (2S) absolute configuration.

Helvetica Chimica Acta published new progress about Alkylation, stereoselective. 172900-69-5 belongs to class bromides-buliding-blocks, name is 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene, and the molecular formula is C17H27BrO3, Safety of 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Lindsay, Karl B. published the artcileFormal Total Synthesis of the Potent Renin Inhibitor Aliskiren: Application of a SmI2-Promoted Acyl-like Radical Coupling, Category: bromides-buliding-blocks, the main research area is renin inhibitor aliskiren total synthesis; samarium diiodide radical addition phenylalanine thioester acrylate.

A formal total synthesis of the potent renin inhibitor aliskiren is disclosed exploiting an alternative coupling strategy recently developed by the authors for the preparation of the hydroxyethylene isostere-based class of protease inhibitors. The 4-pyridyl thioester derivative of amino acid, CbzNHCH(CH2Ph)COS-Pyr (Pyr = 4-pyridyl), representing the C5-C9 fragment of the aliskiren carbon skeleton underwent a carbon chain extension via a SmI2-promoted radical addition to Bu acrylate. Introduction of the C3-iso-Pr group with the correct relative configuration was accomplished via stereoselective reduction of the obtained ketone with concomitant lactonization, followed by an aldol reaction with acetone. Further functional group and protecting group manipulation culminated in a formal total synthesis of aliskiren in 10 steps from the corresponding fully protected non-natural amino acid.

Journal of Organic Chemistry published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 172900-69-5 belongs to class bromides-buliding-blocks, name is 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene, and the molecular formula is C17H27BrO3, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary