185965-95-1Relevant academic research and scientific papers
Copper-Mediated Introduction of the CF2PO(OEt)2 Motif: Scope and Limitations
Ivanova, Maria V.,Bayle, Alexandre,Besset, Tatiana,Pannecoucke, Xavier,Poisson, Thomas
, p. 17318 - 17338 (2017/11/20)
Herein, a general procedure to access CF2PO(OEt)2-containing molecules is reported. The reagent CuCF2PO(OEt)2 is accessible by a simple protocol and a broad range of substrates can be functionalised. The procedure allows the conversion of aryl diazonium salts, as well as aryl, heteroaryl, vinyl and alkynyl iodonium salts, into the corresponding fluorinated molecules at room temperature. Mechanistic studies were performed to gain a better understanding of the reaction pathway. Under similar conditions, vinyl and aryl iodides, allyl halides, and benzyl bromides were also functionalised, and the scope and limitations of the reaction were studied. Finally, the procedure was extended to disulfides to offer new access to SCF2PO(OEt)2-containing molecules.
Copper-Mediated Formation of Aryl, Heteroaryl, Vinyl and Alkynyl Difluoromethylphosphonates: A General Approach to Fluorinated Phosphate Mimics
Ivanova, Maria V.,Bayle, Alexandre,Besset, Tatiana,Poisson, Thomas,Pannecoucke, Xavier
supporting information, p. 13406 - 13410 (2015/11/09)
A general and efficient access to aryl, heteroaryl, vinyl and alkynyl difluoromethylphosphonates is described. The developed methodology using TMSCF2PO(OEt)2, iodonium salts and a copper salt provided a straightforward manifold to re
Copper-mediated synthesis of aryldifluoromethylphosphonates: A sandmeyer approach
Bayle, Alexandre,Cocaud, Chloé,Nicolas, Cyril,Martin, Olivier R.,Poisson, Thomas,Pannecoucke, Xavier
supporting information, p. 3787 - 3792 (2015/06/16)
Difluoromethylated arenes are scaffolds of great interest. We report herein a mild and general method for the introduction of the CF2PO(OEt)2 moiety into arenes. The CuCF2PO(OEt)2 species, which is generated in
Rational design of selective organoruthenium inhibitors of protein tyrosine phosphatase 1B
Ong, Jun Xiang,Yap, Chun Wei,Ang, Wee Han
, p. 12483 - 12492 (2013/01/15)
Protein tyrosine phosphatases (PTPs) belong to a large family of important regulatory enzymes involved in vital mammalian signaling pathways. Selective inhibitors of PTPs are highly valuable from a therapeutic standpoint given their association with various pathological conditions. One such target is PTP-1B which has previously been linked to diabetes and cancer. However, developing a selective inhibitor against PTP-1B has proven to be daunting because the enzyme shares a high degree of structural homology with TC-PTP, an essential PTP involved in modulating immune functions. To address this challenge, a series of organoruthenium complexes was developed to bind at the PTP substrate-binding site while simultaneously target the peripheral structural space. By capitalizing on the potential difference in the structural environment proximal to the active site between different PTPs, selectivity toward PTP-1B over TC-PTP was improved, paving the way for organoruthenium complexes as selective PTP-1B metalloinhibitors.
Structure of protein tyrosine phosphatase 1B in complex with inhibitors bearing two phosphotyrosine mimetics
Jia,Ye,Dinaut,Wang,Waddleton,Payette,Ramachandran,Kennedy,Hum,Taylor
, p. 4584 - 4594 (2007/10/03)
Protein tyrosine phosphatases (PTPases) are signal-transducing enzymes that dephosphorylate intracellular proteins that have phosphorylated tyrosine residues. It has been demonstrated that protein tyrosine phosphatase 1B (PTP1B) is an attractive therapeut
Enzymatic desymmetrization of prochiral 2-benzyl-1,3-propanediol derivatives: A practical chemoenzymatic synthesis of novel phosphorylated tyrosine analogues
Yokomatsu, Tsutomu,Minowa, Takayuki,Murano, Tetsuo,Shibuya, Shiroshi
, p. 9341 - 9356 (2007/10/03)
(Phosphonomethyl)phenylalanine (Pmp) and (phosphonodifluoromethyl)phenylalanine (F2Pmp) as well as their β-amino acid congeners were prepared as a protecting variant amenable to the peptide synthesis from readily available 2-benzyl-1,3-propandiols possessing either a diethylphosphonomethyl- or diethylphosphonodifluoromethyl functionality at the para-position via the lipase-catalyzed desymmetrization.
Synthesis of L-2,3,5,6-tetrafluoro-4-(phosphonomethyl)phenylalanine, a novel non-hydrolyzable phosphotyrosine mimetic and L-4-(phosphonodifluoromethyl)phenylalanine
Liu, Wang-Qing,Roques, Bernard P.,Garbay, Christiane
, p. 1389 - 1392 (2007/10/03)
A new non-hydrolyzable phosphotyrosine analogue, L-F4Pmp and its N-Fmoc protected derivative were prepared by using an enantioselective synthetic pathway with camphor sultam as chiral auxiliary. The side chain pKa2 (6.9) of L-F4
