To investigate a new glycosylation method. Methods In the presence of TMSOTfas catalyst, 1-O-(3, 5-dinitrobenzoyl)-2, 3, 4, 6-tetra-O-benzyl-α-D-glucopyranose 1 reacted with aseries of carboxylic acid, phenols, alcoh...To investigate a new glycosylation method. Methods In the presence of TMSOTfas catalyst, 1-O-(3, 5-dinitrobenzoyl)-2, 3, 4, 6-tetra-O-benzyl-α-D-glucopyranose 1 reacted with aseries of carboxylic acid, phenols, alcohols and saccharides respectively to give the correspondingglycosylation products. The compounds were determined by ~1H NMR and ^(13)C NMR spectra. ResultsThe α-glu-co-pyranosides and related oligosaccharides were prepared in high yields. Conclusion The3, 5-dinitro-benzoyl group was found to be a good leaving group at the anomeric position andO-glucopyranosides and oligosaccharides were stereoselectively synthesized in good yield.展开更多
The title adduct imidazolium 3,5-dinitrobenzoate has been synthesized in aqueous solution and characterized by elemental analyses, IR spectrum and X-ray crystallography. The title compound belongs to monoclinic, space...The title adduct imidazolium 3,5-dinitrobenzoate has been synthesized in aqueous solution and characterized by elemental analyses, IR spectrum and X-ray crystallography. The title compound belongs to monoclinic, space group P21/n with a = 7.5540（9）, b = 21.333（2）, c = 7.7823（9）A, β = 102.741（2）^o, C10H8N4O6, Mr = 280.20, V= 1223.3（2）A^3, Z = 4, Dc = 1.521 g/cm^3, F（000） = 576, p = 0.129 mm^-1, the final R = 0.0433 and wR = 0.1092 for 2001 observed reflections with I 〉 2a（I）. The structural analysis indicates the component ions are linked by N-H...O hydrogen bonds into an infinite one-dimensional C2^2 （8） chain parallel to the [1 0 -1] direction. Moreover, the theoretical investigations of the title compound with HF/6-31G（d） method were performed, and its stability, frontier molecular orbital composition and Mulliken charge distribution were also discussed.展开更多
文摘To investigate a new glycosylation method. Methods In the presence of TMSOTfas catalyst, 1-O-(3, 5-dinitrobenzoyl)-2, 3, 4, 6-tetra-O-benzyl-α-D-glucopyranose 1 reacted with aseries of carboxylic acid, phenols, alcohols and saccharides respectively to give the correspondingglycosylation products. The compounds were determined by ~1H NMR and ^(13)C NMR spectra. ResultsThe α-glu-co-pyranosides and related oligosaccharides were prepared in high yields. Conclusion The3, 5-dinitro-benzoyl group was found to be a good leaving group at the anomeric position andO-glucopyranosides and oligosaccharides were stereoselectively synthesized in good yield.
基金Basic Research Foundation for Natural Science of Henan University (No. 04YBRW053)
文摘The title adduct imidazolium 3,5-dinitrobenzoate has been synthesized in aqueous solution and characterized by elemental analyses, IR spectrum and X-ray crystallography. The title compound belongs to monoclinic, space group P21/n with a = 7.5540（9）, b = 21.333（2）, c = 7.7823（9）A, β = 102.741（2）^o, C10H8N4O6, Mr = 280.20, V= 1223.3（2）A^3, Z = 4, Dc = 1.521 g/cm^3, F（000） = 576, p = 0.129 mm^-1, the final R = 0.0433 and wR = 0.1092 for 2001 observed reflections with I 〉 2a（I）. The structural analysis indicates the component ions are linked by N-H...O hydrogen bonds into an infinite one-dimensional C2^2 （8） chain parallel to the [1 0 -1] direction. Moreover, the theoretical investigations of the title compound with HF/6-31G（d） method were performed, and its stability, frontier molecular orbital composition and Mulliken charge distribution were also discussed.
