118243-90-6Relevant academic research and scientific papers
Synthesis of N-glycoside compounds from phthalimide and 5-nitrobenzimidazole via 1,2-O-sulfinyl derivatives and in vitro cytotoxic activity
Benksim, Abdelhafid,Elhizazi, Said,Lakhrissi, Brahim,Amine, Mohamed,Cherkaoui, Mohamed,Tounsi, Abdessamad,Wadouachi, Anne
, p. 1567 - 1573 (2020)
An efficient synthesis of 1,2-trans-N-glycosylated derivatives from phthalimide and nitrobenzimidazole via 1,2-O-sulfinyl monosaccharides has been established. Such SN2-type displacements at the anomeric center are stereospecific, giving a sing
1,2-Anhydrosaccharides and 1,2-cyclic sulfites as saccharide donors in convergent synthesis of glucopyranosyl-, mannopyranosyl- and ribofuranosylbenzocamalexin
Humenik, Martin,Kutschy, Peter,Kovacik, Vladimir,Bekesova, Slavka
, p. 487 - 506 (2007/10/03)
A convergent synthesis of 1-(β-o-glucopyranosyl)-, 1-(α-D-mannopyranosyl)- and 1-(β-D-ribofuranosyl) benzocamalexin was elaborated as an alternative route to the linear approach based on the indoline-indole method. 1,2-Anhydrosaccharides and 1,2-cyclic sulfites as saccharide donors were used in the key glycosylation step. Coupling with benzocamalexin resulted in moderate to excellent yields of nucleoside analogs, depending on the saccharide donor, catalyst and solvent used.
A novel stereospecific synthesis of glycosyl cyanides from 1,2-O-sulfinyl derivatives
Benksim, Abdelhafid,Beaupere, Daniel,Wadouachi, Anne
, p. 3913 - 3915 (2007/10/03)
(Chemical Equation Presented) An efficient synthesis of 1,2-trans-glycosyl cyanides via 1,2-O-sulfinyl monosaccharides is described. Such S N2-type displacements at the anomeric center are stereospecific and are best performed with sodium cyani
SYNTHESE DE NUCLEOSIDES PYRIMIDIQUES NON PROTEGES EN O-2'A PARTIR DE SULFITES CYCLIQUES EN C-1-C-2
Gagnieu, Christian H.,Guiller, Alain,Pacheco, Henri
, p. 233 - 242 (2007/10/02)
Treatment of 3,5,6-tri-O-benzoyl-α-D-glucofuranose 1,2-sulfite with an excess of bis(trimethylsilyl) uracil, in fusion processes without any catalyst, afforded an excellent yield of 1-(3,5,6-tri-O-benzoyl-2-O-trimethylsilyl-β-D-glucopyranosyl)uracil, which was readily hydrolyzed in slightly acid conditions to give in almost quantitative yield 1-(3,5,6-tri-O-benzoyl-β-D-glucofuranosyl)uracil.This new synthetic method for nucleosides unprotected at O-2' was also tested in other sugar series.In some cases, only the 1',2'-trans-nucleosides were obtained, but in others, small yields (3-10percent) of 1',2'-cis-nucleosides were detected.The α-to-β ratio seems to be dependent on the reaction temperature. 2,4-Dimethoxypyrimidine also reacted with sugar 1,2-sulfites and 4-O-methyl-1-(3,5,6-tri-O-benzyl-β-D-glucopyranosyl)-2-pyrimidinone was prepared in 85percent yield from 3,5,6-tri-O-benzyl-α-D-glucopyranose 1,2-sulfite.
