152871-96-0Relevant academic research and scientific papers
Application of the 2-nitrobenzyl group in glycosylation reactions: A valuable example of an arming participating group
Buda, Szymon,Golebiowska, Patrycja,Mlynarski, Jacek
supporting information, p. 3988 - 3991 (2013/07/19)
The application of the o-nitrobenzyl (oNBn) group is demonstrated. This practical methodology allows the stereocontrolled synthesis of glucosides with a 1,2-trans linkage. This new ether-type arming group can broadly extend the concept of the use of participating groups in glycosylation reactions. Easy protection and deprotection of the oNBn group further confirms its usefulness in synthesis. The application of o-nitrobenzyl (oNBn) ether as an arming participating group is demonstrated. This practical methodology allows the stereocontrolled synthesis of glucosides with a 1,2-trans linkage. Copyright
Synthetic oligosaccharides as tools to demonstrate cross-reactivity between polysaccharide antigens
Pozsgay, Vince,Kubler-Kielb, Joanna,Coxon, Bruce,Santacroce, Paul,Robbins, John B.,Schneerson, Rachel
, p. 5922 - 5941 (2012/10/07)
Escherichia coli O148 is a nonencapsulated enterotoxigenic (ETEC) Gram negative bacterium that can cause diarrhea, hemorrhagic colitis, and hemolytic uremic syndrome in humans. The surface-exposed O-specific polysaccharide (O-SP) of the lipopolysaccharide
Disaccharide-containing macrocycles by click chemistry and intramolecular glycosylation
Tiwari, Vinod K.,Kumar, Amit,Schmidt, Richard R.
supporting information; experimental part, p. 2945 - 2956 (2012/07/27)
In this study o- and m-xylylene moieties in combination with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyra
Stereoselective synthesis of α-glucosides by neighbouring group participation via an intermediate thiophenium ion
Cox, Daniel J.,Fairbanks, Antony J.
experimental part, p. 773 - 780 (2009/09/30)
The use of a 2-O-(thiophen-2-yl)methyl protecting group allows highly stereoselective α-glucosylation of a trichloroacetimidate donor; increased stereoselectivity, presumably arising from the intramolecular formation of a transient intermediate thiophenium ion, correlates with increased bulk of the glycosyl acceptor.
1,2-cis-c-glycoside synthesis by samarium diiodide-promoted radical cyclizations
Skrydstrup, Troels,Mazeas, Daniel,Elmouchir, Mohamed,Doisneau, Gilles,Riche, Claude,Chiaroni, Angele,Beau, Jean-Marie
, p. 1342 - 1356 (2007/10/03)
The samarium diiodide reduction of glycosyl pyridyl sulfones bearing a silicon-tethered unsaturated group at the C2-OH position leads to the stereo-specific synthesis of 1,2-cis-C-glycosides in good yield after desilylation. These reactions proceed via an
SmI2-promoted chemistry at the anomeric center of carbohydrates. Reductive formation and reaction of glycosyl samarium (III) reagents
Pouilly, P. de,Chenede, A.,Mallet, J.-M.,Sinay, P.
, p. 256 - 265 (2007/10/02)
Reaction of 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl chloride at room temperature with the efficient single electron transfer system of SmI2-THF-HMPA, in the presence of cyclopentanone (Barbier conditions) gave selectively the corresponding α-C-glycoside in 70percent yield.It is postulated that the reactive transient intermediate is a chiral anomeric organosamarium (III) species.Lower yields were obtained in the presence of aldehydes, such as n-butanal or isobutanal.It is also demonstrated that glycosyl phenyl sulfones undergo reductive samariation. 2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl phenyl sulfone reacted with cyclopentanone, in the presence of SmI2-THF-HMPA, to give the corresponding β-C-glycoside selectively in 25percent yield, together with the elimination product (40percent).When the protecting group at C-2 was an acetate, a very fast β-elimination of the organosamarium intermediate occurred to give a practically quantitative yield of a substituted glycal.This work constitutes the first application of samarium(II) iodide to the reductive metallation of the anomeric center of carbohydrates.Key words: samarium diiodide / sulfones / carbohydrates / glycals / C-glycosides
