123-34-2Relevant academic research and scientific papers
Synthesis of Phospholipids using an Inverse Phosphite Triester Approach
Hebert, Normand,Just, George
, p. 1497 - 1498 (1990)
1,2-Diacylglycerols, prepared from allyl protected precursors, were transformed into glycerophosphatidylcholines through an acid catalysed coupling with a dialkyl phosphoramidite, followed by a one step deprotection-substitution reaction.
Microwave-assisted, rapid cycloaddition of allyl glycidyl ether and CO 2 by employing pyridinium-based ionic liquid catalysts
Tharun, Jose,Kathalikkattil, Amal Cherian,Roshan, Roshith,Kang, Dong-Heon,Woo, Hee-Chul,Park, Dae-Won
, p. 31 - 34 (2014)
This study investigated the use of pyridinium-based ionic liquids (ILs) as an efficient catalyst for the rapid solvent-free microwave-assisted cycloaddition of allyl glycidyl ether (AGE) and CO2 to yield allyl glycidyl carbonate (AGC) under moderate reaction conditions. The cycloaddition reaction occurred over a short reaction time of 30 s, resulting in a high turnover frequency (TOF) ranging from 200 to 7000 h- 1. The effects of alkyl chain length and anion of pyridinium-based catalysts on the cycloaddition reactivity were studied. The effects of reaction parameters such as the amount of catalyst, microwave power, CO2 pressure, and reaction time were also investigated.
Synthesis of a plasmenylethanolamine
Asano, Yoshio,Enomoto, Masaru,Inoue, Tsubasa,Kuwahara, Shigefumi,Maeda, Satoshi,Mohri, Tomoyo,Nakagawa, Kiyotaka,Ogura, Yusuke,Otoki, Yurika
, p. 1383 - 1389 (2021)
A concise synthesis of a plasmenylethanolamine (PlsEtn-[16:0/18:1 n-9]), known as antioxidative phospholipids commonly found in cell membranes, has been achieved from an optically active known diol through 8 steps. The key transformations for the synthesis of PlsEtn-[16:0/18:1 n-9] are (1) regio- A nd Z-selective vinyl ether formation via the alkylation of a lithioalkoxy allyl intermediate with an alkyl iodide, and (2) a one-pot phosphite esterification-oxidation sequence to construct the ethanolamine phosphonate moiety in the presence of the vinyl ether functionality. The piperidine salt of synthetic PlsEtn-[16:0/18:1 n-9] was desalinated through reversed-phase high-performance liquid chromatography purification.
Discovery of lipids from B. longum subsp. infantis using whole cell MALDI analysis
Timmer, Mattie S. M.,Sauvageau, Janelle,Foster, Amy J.,Ryan, Jason,Lagutin, Kirill,Shaw, Odette,Harper, Jacquie L.,Sims, Ian M.,Stocker, Bridget L.
, p. 7332 - 7341 (2014)
Bifidobacteria are dominant members of the microbial community in the intestinal tract of infants, and studies have shown that glycolipids extracted from the cell surface of these bacteria elicit beneficial immune responses. Accordingly, the identification and structural characterization of glycolipids from the cell wall of bifidobacteria is the first step in correlating glycolipid structure with biological activity. Using whole cell MALDI as a screening tool, we herein present for the first time the identification and structural elucidation of the major polar lipids from Bifidobacterium longum subs. infantis. The lipids identified include an unprecedented plasmenyl cyclophosphatidic acid and a mixed acetal glycolipid, with the latter subsequently being isolated and found to suppress the innate immune response.
Room-temperature self-healing polymers based on dynamic-covalent boronic esters
Cash, Jessica J.,Kubo, Tomohiro,Bapat, Abhijeet P.,Sumerlin, Brent S.
, p. 2098 - 2106 (2015)
Cross-linked polymers constructed with dynamic-covalent boronic esters were synthesized via photoinitiated radical thiol-ene click chemistry. Because the reversibility of the boronic ester cross-links was readily accessible, the resulting materials were capable of undergoing bond exchange to covalently mend after failure. The reversible bonds of the boronic esters were shown to shift their exchange equilibrium at room temperature when exposed to water. Nevertheless, the materials were observed to be stable and hydrophobic and absorbed only minor amounts of water over extended periods of time when submerged in water or exposed to humid environments. The facile reversibility of the networks allowed intrinsic self-healing under ambient conditions. Highly efficient self-healing of these bulk materials was confirmed by mechanical testing, even after subjecting a single site to multiple cut-repair cycles. Several variables were considered for their effect on materials properties and healing, including cross-link density, humidity, and healing time.
Structurally Simple Benzylidene-Type Photolabile Diol Protecting Groups
Ding, Xiong,Devalankar, Dattatray A.,Wang, Pengfei
, p. 5396 - 5399 (2016)
Two structurally simple photolabile protecting groups for releasing 1,2- and 1,3-diols have been developed. The diols can be protected in high yields and released from their corresponding acetals with high chemical efficiency.
Zwitterionic Quaternary Ammonium Alkoxides: Organic Strong Bases
Lovett, Eva G.
, p. 2755 - 2758 (1991)
Stable quaternary ammonium alkoxides, a new type of organic strong base, were obtained from unhindered tertiary alkanolamines and glycidol.At elevated temperatures, the 2-hydroxyethyl derivatives underwent intramolecular rearrangements and deoxyalkylation to form tertiary amine terminated 1,4-poly(3-hydroxyoxetanes).Demethylation was also observed.The 3-hydroxypropyl derivative underwent disproportionation and Hofmann elimination in addition.
Aqueous-microwave synthesized carboxyl functional molecular ribbon coordination framework catalyst for the synthesis of cyclic carbonates from epoxides and CO2
Kathalikkattil, Amal Cherian,Kim, Dong-Woo,Tharun, Jose,Soek, Han-Geul,Roshan, Roshith,Park, Dae-Won
, p. 1607 - 1616 (2014)
A carboxyl-containing coordination polymer catalyst {Cu(Hip) 2(Bpy)}n (CHB) was synthesized rapidly in an aqueous medium using microwave energy and characterized for its structure, morphology, acid-base sites and heterogeneity using experimental and physicochemical techniques. The microwave route was established as competent with the hydrothermal pathway. Exploration of the coordination modes of metal-organic framework (MOF) ligands, especially carboxyl spacers, in achieving reactive functional groups is herein illustrated as crucial rather than focusing merely on the porosity of MOF catalysts. The work represents the first report of a carboxyl-containing MOF class material employed for synthesizing cyclic carbonates from epoxide and CO2. The metal-carboxyl mediated cycloaddition of allyl glycidyl ether and CO2 by the cooperative influence of Cu2+ and the COOH of CHB was synergistically enhanced by an ionic liquid co-catalyst to obtain allyl glycidyl carbonate in 89% yield at optimised reaction conditions. The epoxide substrate scope, effect of reaction parameters and catalyst recyclability (up to 5 cycles) were also studied.
Synthesis and Evaluation of New Polyurethane - Based Material for Ion Separation
Favre-Reguillon, Alain,Dumont, Nathalie,Dunjic, Branko,Lemaire, Marc
, p. 6439 - 6442 (1995)
The polyaddition of macrocyclic diols with diisocyanates is an easy way to prepare ionselective polymers bearing pendant crown ethers.Those polymers can be readily immobilized on silicagel, with no change of ionselective properties.
Aromatic Donor-Acceptor Interaction-Based Co(III)-salen Self-Assemblies and Their Applications in Asymmetric Ring Opening of Epoxides
Liang, Jian,Soucie, Luke N.,Blechschmidt, Daniel R.,Yoder, Aaron,Gustafson, Addie,Liu, Yu
supporting information, p. 513 - 518 (2019/01/14)
Aromatic donor-acceptor interaction as the driving force to assemble cooperative catalysts is described. Pyrene/naphthalenediimide functionalized Co(III)-salen complexes self-assembled into bimetallic catalysts through aromatic donor-acceptor interactions and showed high catalytic activity and selectivity in the asymmetric ring opening of various epoxides. Control experiments, nuclear magnetic resonance (NMR) spectroscopy titrations, mass spectrometry measurement, and X-ray crystal structure analysis confirmed that the catalysts assembled based on the aromatic donor-acceptor interaction, which can be a valuable noncovalent interaction in supramolecular catalyst development.
