120379-76-2

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 603-35-0 triphenylphosphine 
• 627-18-9 1-bromo-3-propanol 
• 89031-84-5 3-(tert-butyldimethylsilyloxy)propyl bromide 
• 51860-45-8 3-hydroxypropyltriphenylphosphonium bromide 

Downstream Products

• 127540-53-8 4-<3,4-bis(octanoyloxy)cyclohexyl>-1-O-(dimethyl-tert-butylsilyl)-3-buten-1-ol 
• 127540-53-8 4-<3,4-bis(octanoyloxy)cyclohexyl>-1-O-(dimethyl-tert-butylsilyl)-3-buten-1-ol 
• 191795-60-5 tert-Butyl-((Z)-7-chloro-hept-3-enyloxy)-dimethyl-silane 
• 191795-63-8 [(Z)-6-(2-Bromo-phenyl)-hex-3-enyloxy]-tert-butyl-dimethyl-silane 
• 928136-83-8 (E/Z)-4-[(4-tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-1-trityl-1H-imidazole 
• 1255955-36-2 (Z,2R,3S,4R)-2,3,4-tris(benzyloxy)-8-t-butyldimethylsilanyloxy-N-methoxyoct-5-enamide 
• 1394257-25-0 (Z)-benzyl 8-(tert-butyldimethylsilyloxy)oct-5-enoate 
• 689258-74-0 (E)-tert-butyl((4-(4-methoxyphenyl)but-3-en-1-yl)oxy)dimethylsilane 
• 496973-06-9 [(3E,5E)-8,8-bis(benzyloxymethyl)undeca-3,5,10-trienyloxy](tert-butyl)dimethylsilane 

Relevant academic research and scientific papers

Access to Enantiopure Advanced Intermediates en Route to Madangamines

The synthesis of enantiopure ABCE and ABCD tetracyclic advanced intermediates en route to madangamine alkaloids and studies for the construction of the triunsaturated 15-membered D ring of madangamine B and the saturated 13-membered D ring of madangamine E are reported.

Synthesis, structural confirmation, and biosynthesis of 22-OH-PD1n-3 DPA?

PD1n-3 DPA belongs to the protectin family of specialized pro-resolving lipid mediators. The protectins are endogenously formed mediators that display potent anti-inflammatory properties and pro-resolving bioactivities and have attracted interest in drug discovery. However, few studies have been reported of the secondary metabolism of the protectins. To investigate the metabolic formation of the putative C22 mono-hydroxylated product, coined 22-OH-PD1n-3 DPA, a stereoselective synthesis was performed. LC/MS-MS data of synthetic 22-OH-PD1n-3 DPA matched the data for the biosynthetic formed product. Cellular studies revealed that 22-OH-PD1n-3 DPA is formed from n-3 docosapentaenoic acid in human serum, and we confirmed that 22-OH-PD1n-3 DPA is a secondary metabolite produced by ω-oxidation of PD1n-3 DPA in human neutrophils and in human monocytes. The results reported are of interest for enabling future structure–activity relationship studies and provide useful molecular insight of the metabolism of the protectin class of specialized pro-resolving mediators.

CATIONIC LIPID

The present invention provides a cationic lipid which is able to be used for nucleic acid delivery to the cytoplasm. A cationic lipid according to the present invention is, for example, a compound represented by formula (1a) or a pharmaceutically acceptable salt thereof. (In formula (1a), each of L1 and L2 independently represent an alkylene group having 3-10 carbon atoms; each of R1 and R2 independently represent an alkyl group having 4-22 carbon atoms or an alkenyl group having 4-22 carbon atoms; X1 represents a single bond or -CO-O-; and ring P represents one of formulae (P-1) to (P-5).)(In formulae (P-1) to (P-5), R3 represents an alkyl group having 1-3 carbon atoms.)

Synthesis of protectin D1 analogs: novel pro-resolution and radiotracer agents

Protectin D1 is a specialized pro-resolving mediator with potent pro-resolving and anti-inflammatory effects in vivo in several human disease models. Herein the preparation of the first synthetic analog of protectin D1, named 22-F-PD1, is presented together with data from in vivo investigations. This analog showed potent pro-resolving and anti-inflammatory properties. These results inspired the preparation of the radiotracer 22-[18F]F-PD1-ME that was used in a positron emission tomography proof of concept study. Altogether, the findings presented contribute to new knowledge on the biomolecular properties of protectin D1 analogs. In addition, an improved formal synthesis of the metabolite 22-OH-PD1 is reported.

HETEROARYL-SUBSTITUTED TRIAZOLES AS APJ RECEPTOR AGONISTS

Compounds of Formula (I) and Formula (II), pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures: where the definitions of the variables are provided herein.

Iron-Nickel Dual-Catalysis: A New Engine for Olefin Functionalization and the Formation of Quaternary Centers

Alkene hydroarylation forms carbon-carbon bonds between two foundational building blocks of organic chemistry: olefins and aromatic rings. In the absence of electronic bias or directing groups, only the Friedel-Crafts reaction allows arenes to engage alkenes with Markovnikov selectivity to generate quaternary carbons. However, the intermediacy of carbocations precludes the use of electron-deficient arenes, including Lewis basic heterocycles. Here we report a highly Markovnikov-selective, dual-catalytic olefin hydroarylation that tolerates arenes and heteroarenes of any electronic character. Hydrogen atom transfer controls the formation of branched products and arene halogenation specifies attachment points on the aromatic ring. Mono-, di-, tri-, and tetra-substituted alkenes yield Markovnikov products including quaternary carbons within nonstrained rings.

A biosynthetically inspired route to substituted furans using the Appel reaction: Total synthesis of the furan fatty acid F5

Appel reaction conditions have been harnessed to affect a mild biosynthetically inspired dehydration of endoperoxides to deliver multi-substituted electron rich furans. Unlike traditional dehydrative procedures, this method is metal and acid free, and can be achieved under redox neutral conditions. It is general for a range of aryl and alkyl substituted endoperoxides, and is functional group tolerant. Furthermore, this procedure has been used to deliver an effective total synthesis of the furan fatty acid (FFA) F5.

ARYLOXYACETYLINDOLES AND ANALOGS AS ANTIBIOTIC TOLERANCE INHIBITORS

The disclosure provides compounds and pharmaceutical compositions of aryloxyacetylindoles compounds and analogs useful for treating chronic and acute bacterial infections. Certain of the compounds are compounds of general Formula (I) (I) or a pharmaceutically acceptable salt or prodrug thereof. Certain compounds of this disclosure are MvfR inhibitors. MvfR inhibitors reduce the formation of antibiotic tolerant bacterial strains and are useful for treating Gram-negative bacterial infections and reducing the virulence of Pseudomonas aeruginosa. Methods of treating bacterial infections in a subject, including Pseudomonas aeruginosa infections, are also provided by the disclosure.

Remote functionalization of C60 with enantiomerically pure cyclo-[2]-malonate tethers bearing C12 and C14 spacers: Synthetic access to bisadducts of C60 with the inherently chiral trans-3 addition pattern

In this Article, we describe the synthesis of two optically pure diols bearing a 1,2-diol moiety masked as an isopropylidene acetal group and long alkyl chains comprised of 12 and 14 carbon atoms, respectively. The synthetic methodology that was developed offers a general way for the synthesis of optically pure diols with long alkyl chains. Diols (-)-4 and (-)-9 were subjected to a condensation reaction with malonyl dichloride to afford two cyclo-[2]-malonate tethers that were separated by column chromatography in optically pure form. The bismalonates (-)-4b and (-)-9b proved to be excellent tethers for the regioselective Bingel functionalization of C60, furnishing in a regioselective manner the corresponding f,sC and f,sA trans-3 bisadducts with low diastereoselectivity but in very good to excellent total yields. In both cases, the formed trans-3 bisadducts were isolated in pure form by simple column chromatography and were fully characterized. The successful acetal deprotection of the synthesized trans-3 bisadducts afforded quantitatively the corresponding polyalcohols, which represent novel chiral fullerene compounds equipped with glycol moieties.

BOTPPI, a new Wittig salt for the synthesis of 12-(S)-hydroxy- eicosatetraenoic acid [12-(S)-HETE]

An efficient route to (Z)-(8-benzyloxy-8-oxooct-3-en-1-yl) triphenylphosphonium iodide, or BOTPPI, is disclosed, complete with full experimental details, NMR spectra, and HRMS data. BOTPPI serves as a surrogate for (Z)-(8-methoxy-8-oxooct-3-en-1-yl)triphe