108646-05-5Relevant articles and documents
Synthetic transformations of higher terpenoids: XXXVI. Synthesis of furanolabdanoid glycoconjugates with a 1,2,3-triazole linker
Kremenko,Kharitonov, Yu. V.,Shul’ts
, p. 35 - 46 (2017)
Procedures have been developed for the synthesis of 16-[(propargyloxy)methyl]- and 7- and 18-(propargyloxy)labda-8(9),13,14-trienes from phlomisoic acid. Copper-catalyzed cycloaddition of the labdanoid alkynes to azido derivatives of α-D-glucose, D-galactose, D-xylose, and L-arabinose afforded the corresponding N-glycosyl-1,2,3-triazole conjugates.
Design, synthesis and molecular docking analysis of flavonoid derivatives as potential telomerase inhibitors
Cheng, Mao-Sheng,Fan, Zhan-Fang,Fu, Ya,Ho, Sai-Tim,Hu, Chun,Liu, Yang,Shaw, Pang-Chui,Wang, Jian,Wen, Rui,Zhang, Lei
, (2019)
Based on the structural scaffolds of natural products, two series of flavonoid derivatives, for a total of twelve compounds, were designed and synthesized as potential human telomerase inhibitors. Using a modified TRAP-PCR assay, compound 5c exhibited the most potent inhibitory activity against human telomerase with an IC50 value of less than 50 μM. In vitro, the results demonstrated that compound 5c had potent anticancer activity against five classes of tumor cell lines. The molecular docking and molecular dynamics analyses binding to the human telomerase holoenzyme were performed to elucidate the binding mode of active compound 5c. This finding helps the rational design of more potent telomerase inhibitors based on the structural scaffolds of natural products.
Arabinose based gelators: Rheological characterization of the gels and phase selective organogelation of crude-oil
Rajkamal,Pathak, Navendu Prakash,Chatterjee, Debnath,Paul, Abhijit,Yadav, Somnath
, p. 92225 - 92234 (2016)
Oil-spills, whether marine or terrestrial, result in major devastation to the environment and ecosystem, loss of habitat and damage to the economy. While inevitable in the current scenario, oil spillages necessitate prompt remedial action to limit the damage caused. A recent strategy towards this is to congeal the spilled oil into a gel through gelation (for terrestrial oil-spills) or through Phase Selective Organogelation (PSOG) for marine oil-spills which can stem the spread of the oil and also provide for the easy removal and reclamation of the gelled oil. Herein, we report two triazolylarabinoside derivatives that are stable, completely insoluble in water and can carry out the gelation as well as the PSOG of hydrocarbon based organic solvents, petrol, diesel and also crude-oil. The gels have been characterized thoroughly by optical microscopy, FESEM, AFM, XRD and rheological experiments. The gelation of crude-oil has also been unequivocally established via rheological studies. The easily synthesized and cheap triazolylarabinosides could provide simple gelators for the remediation of marine/terrestrial oil-spills.
Stereospecific synthesis of sugar-1-phosphates and their conversion to sugar nucleotides
Timmons, Shannon C.,Jakeman, David L.
, p. 865 - 874 (2008)
As Leloir glycosyltransferases are increasingly being used to prepare oligosaccharides, glycoconjugates, and glycosylated natural products, efficient access to stereopure sugar nucleotide donor substrates is required. Herein, the rapid synthesis and purification of eight sugar nucleotides is described by a facile 30 min activation of nucleoside 5′-monophosphates bearing purine and pyrimidine bases with trifluoroacetic anhydride and N-methylimidazole, followed by a 2 h coupling with stereospecifically prepared sugar-1-phosphates. Tributylammonium bicarbonate and tributylammonium acetate were the ion-pair reagents of choice for the C18 reversed-phase purification of 6-deoxysugar nucleotides, and hexose or pentose-derived sugar nucleotides, respectively.
GUAIANOLIDE α-ARABINOPYRANOSIDES FROM HELENIUM AMARUM
Bohlmann, Ferdinand,Misra, Laxmi N.,Jakupovic, Jasmin,King, Robert M.,Robinson, Harold
, p. 1315 - 1318 (1985)
Key Word Index - Helenium amarum; Compositae; sesquiterpene lactones; pseudoguaianolides; guaianolide-α-arabinopyranosides; sesquiterpenes;seco-caryophyllenes; phenylpropane derivatives. - The aerial parts of Helenium amarum afforded, in addition to compounds reported previously, several known sesquiterpene lactones as well as some new ones, two pseudoguaianolides and a complex mixture of guaianolide α-arabinopyranosides, which differed in the position of the double bond, the configuration at C-8 and the position of an acetate group in the sugar moiety.Furthermoreseco-caryophyllenes and phenylpropane derivatives were isolated.The structures were elucidated by spectroscopic methods and few chemical transformations.
S-Adamantyl Group Directed Site-Selective Acylation: Applications in Streamlined Assembly of Oligosaccharides
Blaszczyk, Stephanie A.,Xiao, Guozhi,Wen, Peng,Hao, Hua,Wu, Jessica,Wang, Bo,Carattino, Francisco,Li, Ziyuan,Glazier, Daniel A.,McCarty, Bethany J.,Liu, Peng,Tang, Weiping
, p. 9542 - 9546 (2019)
The site-selective functionalization of carbohydrates is an active area of research. Reported here is the surprising observation that the sterically encumbered adamantyl group directed site-selective acylation at the C2 position of S-glycosides through dispersion interactions between the adamantyl C?H bonds and the π system of the cationic acylated catalyst, which may have broad implications in many other chemical reactions. Because of their stability, chemical orthogonality, and ease of activation for glycosylation, the site-selective acylation of S-glycosides streamlines oligosaccharide synthesis and will have wide applications in complex carbohydrate synthesis.
DMF promoted xylosylation of terpenols
Satgé, Céline,Le Bras, Jean,Hénin, Fran?oise,Muzart, Jacques
, p. 8405 - 8409 (2005)
The glycosidation of 2,3,4-triacetyl-1-bromo-α-d-xylopyranose with various terpenols occurs at 50°C in DMF without the requirement of any additive. The decisive role of DMF as solvent on the coupling efficiency is highlighted.
The total synthesis of eleutherobin: A surprise ending
Chen, Xiao-Tao,Zhou, Bishan,Bhattacharya, Samit K.,Gutteridge, Clare E.,Pettus, Thomas R. R.,Danishefsky, Samuel J.
, p. 789 - 792 (1998)
An 'sp2-sp3 Stille coupling' of the vinyl triflate 1 and the stannyl compound 2 is a key step toward the completion of the total synthesis of eleutherobin, a natural product exhibiting taxol-like cytotoxic activity.
Stereoselective synthesis of α- And β-glycofuranosyl amides by traceless ligation of glycofuranosyl azides
Nisic, Filippo,Speciale, Gaetano,Bernardi, Anna
, p. 6895 - 6906 (2012)
A highly stereoselective synthesis of α- or β-glycofuranosyl amides based on the traceless Staudinger ligation of glycofuranosyl azides of the galacto, ribo, and arabino series with 2-diphenylphosphanyl-phenyl esters has been developed. Both α- and β-isomers can be obtained with excellent selectivity from a common, easily available precursor. The process does not depend on the anomeric configuration of the starting azide but appears to be controlled by the C2 configuration and by the protection/deprotection state of the substrates. A mechanistic interpretation of the results, supported by 31P NMR experiments, is offered and merged with our previous mechanistic analysis of pyranosyl azide ligation reactions. Copyright
Streamlined synthesis of per-O-acetylated sugars, glycosyl iodides, or thioglycosides from unprotected reducing sugars
Mukhopadhyay, Balaram,Kartha, K.P. Ravindranathan,Russell, David A.,Field, Robert A.
, p. 7758 - 7760 (2004)
Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.
