64214-56-8Relevant academic research and scientific papers
Investigating Bicyclobutane-Triazolinedione Cycloadditions as a Tool for Peptide Modification
Schwartz, Brett D.,Smyth, Aidan P.,Nashar, Philippe E.,Gardiner, Michael G.,Malins, Lara R.
supporting information, p. 1268 - 1273 (2022/02/07)
Acyl bicyclobutanes are shown to engage in strain-promoted cycloaddition reactions with a diverse array of triazolinedione reagents. The synthesis of an orthogonally protected urazole building block enabled the facile preparation of amino acid- and peptid
IONIZABLE CATIONIC LIPID FOR RNA DELIVERY
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, (2018/07/04)
What is described is a compound of formula I consisting of a compound in which R1 is a branched chain alkyl consisting of 10 to 31 carbons; R2 is a linear alkyl, alkenyl, or alkynyl consisting of 2 to 20 carbons; L1 and L2 are the same or different, each a linear alkylene of 1 to 20 carbons or a linear alkenylene of 2 to 20 carbons; X1 is S or O; R3 is a linear or branched alkylene consisting of 1 to 6 carbons; and R4 and R5 are the same or different, each a hydrogen or a linear or branched alkyl consisting of 1 to 6 carbons; or a pharmaceutically acceptable salt thereof.
IONIZABLE CATIONIC LIPID FOR RNA DELIVERY
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Paragraph 0190; 0191; 0192; 0193; 0194, (2018/07/05)
What is described is a compound of formula I consisting of a compound in which R1 is a branched chain alkyl consisting of 10 to 31 carbons;R2 is a linear alkyl, alkenyl, or alkynyl consisting of 2 to 20 carbons, or a branched chain alkyl consisting of 10 to 31 carbons;L1 and L2 are the same or different, each a linear alkane of 1 to 20 carbons or a linear alkene of 2 to 20 carbons;X1 is S or O;R3 is a linear or branched alkylene consisting of 1 to 6 carbons; andR4 and R5 are the same or different, each a hydrogen or a linear or branched alkyl consisting of 1 to 6 carbons; or a pharmaceutically acceptable salt thereof.
Strategic Application and Transformation of ortho-Disubstituted Phenyl and Cyclopropyl Ketones to Expand the Scope of Hydrogen Borrowing Catalysis
Frost, James R.,Cheong, Choon Boon,Akhtar, Wasim M.,Caputo, Dimitri F. J.,Stevenson, Neil G.,Donohoe, Timothy J.
supporting information, p. 15664 - 15667 (2016/01/09)
The application of an iridium-catalyzed hydrogen borrowing process to enable the formation of α-branched ketones with higher alcohols is described. In order to facilitate this reaction, ortho-disubstituted phenyl and cyclopropyl ketones were recognized as crucial structural motifs for C-C bond formation. Having optimized the key catalysis step, the ortho-disubstituted phenyl products could be further manipulated by a retro-Friedel-Crafts acylation reaction to produce synthetically useful carboxylic acid derivatives. In contrast, the cyclopropyl ketones underwent homoconjugate addition with several nucleophiles to provide further functionalized branched ketone products.
A facile synthesis of 5,5-dideutero-4-dimethyl(phenyl)silyl-6-undecyl- tetrahydropyran-2-one as a deuterium labeled synthon for (-)-tetrahydrolipstatin and (+)-δ-hexadecanolide
Wagh, Sandip J.,Chowdhury, Raghunath,Mukhopadhyay, Sulekha,Ghosh, Sunil K.
, p. 649 - 654 (2014/01/06)
Deuterium-labeled biologically active compounds are gaining importance because they can be utilized as tracers or surrogate compounds to understand the mechanism of action, absorption, distribution, metabolism, and excretion. Deuterated drug molecules (heavy drugs) become novel as well as popular because of better stability and bioavailability compared with their hydrogen analogs. Labeling of organic molecules with deuterium at specific positions is thus gaining popularity. In this work, we have exploited a highly regioselective and enantioselective direct Michael addition of methyl-d3 alkyl ketones to dimethyl(phenyl)silylmethylene malonate that was catalyzed by (S)-N-(2-pyrrolidinylmethyl)pyrrolidine/trifluoroacetic acid/ D2O combination with high yield and isotopic purity. The 5,5-dideutero-4- dimethyl(phenyl)silyl-6-undecyl-tetrahydropyran-2-one was obtained from the adduct of methyl-d3 undecanyl ketone and dimethyl(phenyl) silylmethylene malonate by a silicon controlled diastereoselective ketone reduction, lactonization, and deethoxycarbonylation. The dideuterated silylated tetrahydropyran-2-one is the precursor for geminal 2H 2-labeled (+)-4-hydroxy-6-undecyl-tetrahydropyran-2-one, an advanced intermediate for gem-dideutero (-)-tetrahydrolipstatin and (+)-δ- hexadecanolide syntheses. Copyright
Synthesis of functionalised 4H-quinolizin-4-ones via tandem Horner-Wadsworth-Emmons olefination/cyclisation
Muir, Calum W.,Kennedy, Alan R.,Redmond, Joanna M.,Watson, Allan J. B.
supporting information, p. 3337 - 3340 (2013/06/05)
4H-Quinolizin-4-ones are a unique class of heterocycle with valuable physicochemical properties and which are emerging as key pharmacophores for a range of biological targets. A tandem Horner-Wadsworth-Emmons olefination/cyclisation method has been developed to allow facile access to substituted 4H-quinolizin-4-ones encoded with a range of functional groups.
A flexible asymmetric synthesis of the tetracyclic core of berkelic acid using a Horner-Wadsworth-Emmons/oxa-Michael cascade
Wilson, Zoe E.,Brimble, Margaret A.
supporting information; experimental part, p. 1284 - 1286 (2010/06/13)
The one-pot Horner-Wadsworth-Emmons/oxa-Michael cascade followed by spiroketalisation affords the tetracyclic benzannulated spiroketal core of berkelic acid, an extremophile natural product with selective activity against ovarian cancer.
Synthesis and evaluation of novel pyrazolidinone analogs of PGE2 as EP2 and EP4 receptors agonists
Zhao, Zhong,Araldi, Gian Luca,Xiao, Yufang,Reddy, Adulla P.,Liao, Yihua,Karra, Srinivasa,Brugger, Nadia,Fischer, David,Palmer, Elizabeth
, p. 6572 - 6575 (2008/09/16)
Replacement of the hydroxy cyclopentanone ring in PGE2 with chemically more stable heterocyclic rings and substitution of the unsaturated α-alkenyl chain with a metabolically more stable phenethyl chain led to the development of potent and selective analogs of PGE2. Compound 10f showed the highest potency and selectivity for EP4 the receptor.
Synthesis and application of N-methoxy-N-methyl-2-phenylsulfonyl- acetamide as a two-carbon homologating agent
Satyamurthi,Singh, Jaimala,Aidhen, Indrapal Singh
, p. 375 - 382 (2007/10/03)
With the well-known precedence that N-methoxy-N-methyl amides are excellent acyl cation and aldehyde equivalents, N-methoxy-N-methyl-2- phenylsulfonylacetamide (3), a new reagent, synthetically equivalent to ΘCH2CHO and ΘCH2COR was synthesised. The simplicity involved in the alkylation at the active methylene site in 3, followed by safe removal of the phenylsulfonyl group, makes 3 a versatile reagent for two-carbon homologation of alkyl halides. The method, when applied to sugar halides 6j and 6k led to the synthesis of 2,3-dideoxy sugars.
One-pot synthesis of ketones using N-methoxy-N-methyl-2-pyridyl urethane
Lee, Na Ra,Lee, Jae In
, p. 1249 - 1255 (2007/10/03)
The one-pot reaction of N-methoxy-N-methyl-2-pyridyl urethane with Grignard and organolithium reagents provided an efficient method for the preparation of unsymmetrical ketones.
