86534-11-4Relevant articles and documents
Synthesis of tri-arylated cyclotriveratrilenes with ortho- and meta-extended functionality
Ito, Kouhei,Schramm, Michael P.,Kanaura, Mao,Ide, Masataka,Endo, Naoki,Iwasawa, Tetsuo
, p. 233 - 236 (2016)
Aromatic nucleophilic substitution reaction between cyclotriguaiacylene and ortho- or meta-functionalized fluoroarenes affords a series of ortho- or meta-extended cyclotriveratrilene (CTV) cavitands. Further transformation of the functional groups into NH
Molecular recognition by a novel boronate-containing CTG derivative for hydroxyanthraquinones
Inoue, Tsubasa,Moriuchi-Kawakami, Takayo,Kuda, Kentaro,Matsubara, Shota,Fujimori, Keiichi,Moriuchi, Toshiyuki
, p. 2330 - 2335 (2019)
C3-functionalized cyclotriguaiacylene (CTG) derivatives were employed in the development of highly selective recognition compounds due to their unique molecular structures. Here, a novel C3-functionalized CTG containing boronate (PPB
A tris(benzyltriazolemethyl)amine-based cage as a CuAAC ligand tolerant to exogeneous bulky nucleophiles
Qiu, Gege,Nava, Paola,Martinez, Alexandre,Colomban, Cédric
supporting information, p. 2281 - 2284 (2021/03/09)
The archetypal tris(benzyltriazolemethyl)amine (TBTA) ligand was equipped with a bowl-shaped cap in the cage Hm-TBTA. Hm-TBTA accelerates CuAAC reactions without suffering from product inhibition. Furthermore, this shielded ligand efficiently protects the
Enantiopure C1-Cyclotriveratrylene with a Reversed Spatial Arrangement of the Substituents
Long, Augustin,Colomban, Cedric,Jean, Marion,Albalat, Muriel,Vanthuyne, Nicolas,Giorgi, Michel,Di Bari, Lorenzo,Górecki, Marcin,Dutasta, Jean-Pierre,Martinez, Alexandre
supporting information, p. 160 - 165 (2019/01/04)
Cyclotriveratrylene (CTV) is a macrocyclic cyclophane presenting a bowl-shaped conformation, used as building block to construct cryptophane and hemicryptophane capsules. A method to synthesize new enantiopure CTV derivatives with an unprecedented spatial
Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides
Ong, Derek Yiren,Yen, Zhihao,Yoshii, Asami,Revillo Imbernon, Julia,Takita, Ryo,Chiba, Shunsuke
supporting information, p. 4992 - 4997 (2019/03/13)
New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH2)∞ is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H?Zn?Cl)2 is the key species for the production of amines.
Synthesis of Cyclotriveratrylene-Sucrose-Based Capsules
Szyszka, ?ukasz,Cmoch, Piotr,Butkiewicz, Aleksandra,Potopnyk, Mykhaylo A.,Jarosz, S?awomir
supporting information, p. 6523 - 6528 (2019/08/28)
Cyclotriveratrylene (CTV) is a C3-symmetrical macrocycle, which can be used as a chiral building block in the construction of supramolecular containers. Coupling of the CTV unit with a sucrose molecule gave enantiopure water-soluble (after depr
Highly efficient Tsuji-Trost allylation in water catalyzed by Pd-nanoparticles
Llevot,Monney,Sehlinger,Behrens,Meier
supporting information, p. 5175 - 5178 (2017/07/12)
Palladium nanoparticles stabilized by poly(vinylpyrrolidone) catalyze Tsuji-Trost allylations in water with very high turnover numbers. The di-allylation of methylene active compounds and the allylation of bio-based phenols was performed in high yield. The allylation of lignin showed a high selectivity towards the phenolic OH groups.
An orthogonally protected CycloTriVeratrylene (CTV) as a highly pre-organized molecular scaffold for subsequent ligation of different cyclic peptides towards protein mimics
Longin, Ond?ej,van de Langemheen, Helmus,Liskamp, Rob M.J.
, p. 5008 - 5015 (2017/09/19)
The synthesis of a semi-orthogonally protected CycloTriVeratrilene (CTV) scaffold derivative as well as the sequential introduction of three different peptide loops onto this molecular scaffold via Cu(I)-catalyzed azide alkyne cycloaddition towards a medium-sized protein mimic is described. This approach for the construction of medium-sized protein mimics is illustrated by the synthesis of a paratope mimic of the monoclonal antibody Infliximab (Remicade) and provides access to a range of highly pre-organized molecular constructs bearing three different peptide segments. This approach may find wide applications for development of protein-protein interaction disruptors as well as synthetic vaccines.
Vanillin and o-vanillin oligomers as models for dendrimer disassembly
Kevwitch, Robert M.,Shanahan, Charles S.,McGrath, Dominic V.
experimental part, p. 492 - 505 (2012/03/22)
Linear analogs have been synthesized to model disassembling dendrimers. These linear analogs provide a facile synthesis to molecules that can be used to test new trigger groups and cleavage vectors. Vanillin and o-vanillin were used as the monomer units of these analogs and two trigger groups, allyl and o-nitrobenzyl, were chosen to test the disassembly process. Allyl triggered analogs 1a-d and 3a-d and o-nitrobenzyl triggered analogs 2a-c and 4a-c showed good to excellent disassembly as followed by the evolution of p-nitrophenoxide reporter ion by UV-Visible spectroscopy. The rate and yield of disassembly was shown to depend on experimental conditions as well as length of the cleavage vector.
Improved iterative synthesis of linearly disassembling dendrons
Ortiz, Adrian,Shanahan, Charles S.,Sisk, David T.,Perera, Sujeewa C.,Rao, Pallavi,McGrath, Dominic V.
experimental part, p. 6154 - 6162 (2010/11/04)
Figure presented. We report a significant improvement in the synthesis of disassembling dendritic structures by using 4-hydroxy-3-nitrobenzoic acid as the building block. We have prepared multigram quantities of first- through third-generation linearly disassembling dendrons containing a [3-N,4-O]-benzylaryl ether disassembly pathway, capped by a vanillin-derived phenyl allyl ether trigger, and a p-nitrophenoxy (PNP) reporter group. The disassembly process of these materials was initiated by allyl deprotection and monitored by the absorbance of the PNP reporter unit in the UV-vis. Modification of the disassembly conditions for the allyl trigger resulted in decreased disassembly times, decreased incubation time for onset of disassembly from minutes to seconds, and allowed observation of indicative rate differences between generations not seen with the previously reported conditions.
