118243-91-7Relevant academic research and scientific papers
A novel stereospecific synthesis of glycosyl cyanides from 1,2-O-sulfinyl derivatives
Benksim, Abdelhafid,Beaupere, Daniel,Wadouachi, Anne
, p. 3913 - 3915 (2004)
(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
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 (2020/03/03)
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-Cyclic sulfite and sulfate furanoside diesters: improved syntheses and stability
Hardacre, Christopher,Messina, Ivano,Migaud, Marie E.,Ness, Kerry A.,Norman, Sarah E.
experimental part, p. 6341 - 6347 (2009/12/04)
The facile syntheses of 1,2- and 3,5-cyclic sulfite and sulfate furanoside diesters were conducted in molecular solvents and ionic liquids in the presence of immobilised morpholine. Molecular solvents and ionic liquids performed similarly with regards to overall yields. However, the use of ILs allowed for the reactions to be carried out under atmospheric conditions and showed good recyclability. Additionally, increases in product stability was achieved in ILs over organic solvents, in particular, in bis{(trifluoromethanesulfonyl)imide} and trispentafluoro-ethyltrifluorophosphate-based ionic liquids, which were also excellent media to control the hydrolysis of thionyl chloride and sulfuryl chloride.
Efficient O-glycosylation of diethyl oxoglutarate via 1,2-O-sulfinyl derivatives
Benksim, Abdelhafid,Massoui, Mohamed,Beaupère, Daniel,Wadouachi, Anne
, p. 5087 - 5089 (2008/02/09)
1,2-O-Sulfinyl derivatives of d- and l-arabinose, d-xylose and d-glucose treated by potassium anion of diethyl oxoglutarate gave, exclusively, the corresponding O-glycosides in 92-97% yields.
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.
