4468-72-8Relevant articles and documents
DETOXIFICATION OF PHENOL BY THE AQUATIC ANGIOSPERM, Lemna gibba
Barber, John T.,Sharma, Hari A.,Ensley, Harry E.,Polito, Michael A.,Thomas, Dana A.
, p. 3567 - 3574 (1995)
Lemna gibba was used to study the toxicity and metabolism of phenol. The toxicities of phenol and its major metabolite were described in terms of the effect of increasing concentrations on the vegetative reproduction of duckweed over a 7-day growth period
Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature
Verdelet, Tristan,Benmahdjoub, Sara,Benmerad, Belkacem,Alami, Mouad,Messaoudi, Samir
supporting information, p. 9226 - 9238 (2019/08/12)
Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including α-mannose, and it was demonstrated here how the interaction between carbohydrates and boronic acids can be combined with copper catalysis to achieve selective anomeric O-arylation.
Phenyl glycosides – Solid-state NMR, X-ray diffraction and conformational analysis using genetic algorithm
Wa?ejko, Piotr,Bukowicki, Jaros?aw,Dobrzycki, ?ukasz,Socha, Pawe?,Paradowska, Katarzyna
, p. 126 - 136 (2019/01/03)
The X-ray structures of 2,6-dimethylphenyl and phenyl 2,3,4,6-tetra-O-acetyl β-glucosides (1 and 3) and phenyl α-mannoside (6) were obtained. The independent part of the unit cell of the glycosides 1 and 6 was formed by one molecule, and for the glucoside 3, two molecules in the crystal cell were observed. In deacetylated glycosides 4 and 6 the crystal structure was established by a hydrogen bond network formed between the sugar hydroxyls and solvent molecules. The 13C CPMAS NMR spectra of aryl glycosides 1–6 were analysed. In the spectrum of 3, doubling of the C4 aryl signal was observed which confirmed the presence of two independent molecules in the solid sample. The GAAGS (Genetic Algorithm-Assisted Grid Search) method was used to determine the low-energy conformers of α-mannosides and β-glucosides. The orientation of the aryl pendant group was calculated using Molecular Mechanics (MMFF94) as well as Quantum Mechanics theory (DFT, B3LYP/6-31 + G(d,p)).
Revisit of the phenol O-glycosylation with glycosyl imidates, BF 3·OEt2 is a better catalyst than TMSOTf
Li, Yali,Mo, Huaping,Lian, Gaoyan,Yu, Biao
, p. 14 - 22 (2013/01/15)
With BF3·OEt2 as the catalyst, the glycosylation of phenols with glycosyl trichloroacetimidates (or N-phenyl trifluoroacetimidates) bearing 2-O-participating groups leads to the desired 1,2-trans-O-glycosides in generally excellent yields without formation of the 1,2-cis-anomers. However, with TMSOTf as the catalyst, the outcomes of the corresponding phenol O-glycosylation are highly dependent on the nucleophilicity of the phenols; less nucleophilic is the phenol, higher amounts of the 1,2-cis-O-glycoside together with more side-products are generated. 1,2-Orthoesters have been found to be the major products at a low temperature (a higher temperature. BF 3·OEt2 is an effective catalyst to promote the conversion of 1,2-orthoesters into the corresponding 1,2-trans-O-glycosides. However, the 1,2-orthoesters could be converted into the dioxolenium triflate and glycosyl triflate in the presence of TMSOTf, these intermediates which might be in equilibrium with the glycosyl oxocarbenium related species lead to the final mixture of the α/β-O-glycosides and side-products.
