3081-28-5Relevant academic research and scientific papers
Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts
Rull, Jordi,Jara, José Juan,Sebastián, Rosa M.,Vallribera, Adelina,Nájera, Carmen,Majoral, Jean-Pierre,Caminade, Anne-Marie
, p. 2049 - 2056 (2016/07/07)
Four new phosphorus dendrimeric phase-transfer catalysts are prepared that contain 12 (+)-cinchoninium salts on the surface obtained by the quaternisation of the quinuclidinic N atom. The asymmetric alkylation of a glycinate Schiff base with benzyl bromide is used as a benchmark reaction, and the dendrimeric catalyst that contains an allyl group on the O-9 hydroxy group of the cinchonine units is the most active. The recovery and reuse of the catalyst are possible for five consecutive runs without loss of activity and with only a slight decrease in enantioselectivity. If other electrophiles are used, substituted benzyl bromides give better results than other activated alkyl bromides to afford the corresponding R amino acid derivatives. A comparison of these results with those reported previously for similar cinchoninium salts shows that dendrimers could be a better support than other polymers for this type of organocatalysis.
An efficient asymmetric biomimetic transamination of α-keto esters to chiral α-amino esters
Xiao, Xiao,Liu, Mao,Rong, Chao,Xue, Fazhen,Li, Songlei,Xie, Ying,Shi, Yian
supporting information, p. 5270 - 5273 (2013/01/15)
An efficient asymmetric biomimetic transamination of α-keto esters with quinine derivatives as chiral bases was described. A wide variety of α-amino esters containing various functional groups can be synthesized in high yield and enantioselectivity.
MODULATORS OF TLR3/DSRNA COMPLEX AND USES THEREOF
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Page/Page column 23, (2012/08/07)
The present invention provides compounds and compositions that can modulate formation of Toll-like receptor 3 (TLR3) and double-stranded RNA (dsRNA) complex, and methods for using the same. In particular, some aspects of the invention provide compounds of the formula (I) compositions comprising and methods for using the same, where n, Ar1, Ar2, X1, X2, X3, Z1, and Z2 are those defined herein.
C2-symmetric pyrrolidine-based chiral ammonium salts as a phase-transfer catalyst
Ishikawa, Tatsuya,Nagata, Kazuhiro,Kani, Sachiko,Matsuo, Mamoru,Sano, Daisuke,Kanemitsu, Takuya,Miyazaki, Michiko,Itoh, Takashi
experimental part, p. 2577 - 2588 (2012/01/06)
Chiral pyrrolidinium salts having substituents at the α, α' positions were synthesized to develop a chiral phase-transfer catalyst which have more simplified structure. The catalytic function of these synthesized catalysts was evaluated using asymmetric b
A practical large-scale synthesis of cyclic RGD pentapeptides suitable for further functionalization through click' chemistry
Palecek, Jiri,Draeger, Gerald,Kirschning, Andreas
experimental part, p. 653 - 661 (2011/04/15)
A multigram batch of the cyclo[Arg-Gly-Asp-d-Phe-Lys] and its N - azido derivative was accomplished via solution-phase synthesis using an epimerization-free fragment condensation. The C-terminus of d-Phe was protected as its tert-butyl ester. Fmoc (Arg, Gly, Asp, d-Phe) and Boc (Lys) groups were used to protect all N - termini. The Ts and NO2 groups, respectively were chosen to protect the guanidine group. The macrocyclization step (between d-Phe and l-Lys) was carried out under TBTU/HOBt or DPPA condensation conditions. Finally, the -amino group of the lysine residue was selectively converted into the azido group by a diazo-transfer reaction. Georg Thieme Verlag Stuttgart New York.
Small-molecule inhibitors of the TLR3/dsRNA complex
Cheng, Kui,Wang, Xiaohui,Yin, Hang
supporting information; experimental part, p. 3764 - 3767 (2011/06/18)
The protein-RNA interface has been regarded as "undruggable" despite its importance in many biological processes. The toll-like receptor 3 (TLR3)/double-stranded RNA (dsRNA) complex provides an exciting target for a number of infectious diseases and cancers. We describe the development of a series of small-molecule probes that were shown to be competitive inhibitors of dsRNA binding to TLR3 with high affinity and specificity. In a multitude of assays, compound 4a was profiled as a potent antagonist to TLR3 signaling and also repressed the expression of downstream signaling pathways mediated by the TLR3/dsRNA complex, including TNF-α and IL-1β.
A bismuth(III)-catalyzed friedel-crafts cyclization and stereocontrolled organocatalytic approach to (-)-platensimycin
Eey, Stanley T.-C.,Lear, Martin J.
, p. 5510 - 5513 (2011/03/18)
A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)3 to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promoted cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.
Enzymatic synthesis of carnosine derivatives catalysed by Burkholderia cepacia lipase
D'Arrigo, Paola,Kanerva, Liisa T.,Li, Xiang-Guo,Saraceno, Caterina,Servi, Stefano,Tessaro, Davide
experimental part, p. 1641 - 1645 (2009/12/04)
A new enzymatic synthesis of α,β-dipeptides has been developed with particular focus on the preparation of carnosine (β-alanyl-α-histidine) and analogues. The lipase PS-D from Burkholderia cepacia has been used as a catalyst for the formation of the pepti
PROCESS FOR PRODUCTION OF MONO-SUBSTITUTED ALKYLATED COMPOUND USING ALDIMINE OR DERIVATIVE THEREOF
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Page/Page column 109, (2008/06/13)
Disclosed is a process for producing an asymmetric mono-substituted alkylated compound of an α-amino acid which is represented by a specific formula by using an aldimine-type Schiff base. In the process, the alkylation of an aldimine-type Schiff base in a medium in the presence of an optically active quaternary ammonium salt phase transfer catalyst and an inorganic base is started, and subsequently the reaction is quenched at any time preceding the completion of the stoichimetrical reaction, thereby yielding a mono-substituted alkylated product having a high optical purity.
Structure-selectivity studies on catalysts for the phase-transfer catalysed asymmetric alkylation of glycine imine esters
Lygo,Crosby,Lowdon,Wainwright
, p. 2391 - 2402 (2007/10/03)
In this paper, we describe the synthesis of a series of chiral quaternary ammonium salts with core structures that are closely related to the cinchona alkaloid, cinchonine. By employing these salts as asymmetric phase-transfer agents in the benzylation of a glycine imine, an optimal catalyst structure is identified.
