Showing papers by "Jianbo Zhang published in 2017"
TL;DR: A facile and direct O -glycosylation method for the stereoselective synthesis of 2,6-dideoxy α-O -aryl-glycosides has been described using an eco-friendly catalyst, ferric chloride (FeCl 3 ).
Abstract: A facile and direct O -glycosylation method for the stereoselective synthesis of 2,6-dideoxy α- O -aryl-glycosides has been described using an eco-friendly catalyst, ferric chloride (FeCl 3 ). The approach can be applied to a wide range of differently substituted phenols including not only mono-substituted ones bearing electron-donating and electron-withdrawing groups but also disubstituted ones. Ultimately, 2,6-dideoxy aryl- O -glycosides were obtained rapidly (
9 citations
TL;DR: A metal free and highly stereoselective procedure for the synthesis of 2,3-unsaturated-C-glycosides has been developed between glycals and unactivated aryl acetylenes in the presence of TMSOTf through a triflated C-vinyl glycosides intermediate.
Abstract: A metal free and highly stereoselective procedure for the synthesis of 2,3-unsaturated-C-glycosides has been developed between glycals and unactivated aryl acetylenes in the presence of TMSOTf through a triflated C-vinyl glycosides intermediate. The flexibility of the procedure was tested by a wide variety of glycals and unactivated aryl acetylenes (20 examples). The corresponding alkynyl C-glycosides were obtained in good yields with completely α-selectivity in a short time (<25 min). And a plausible mechanism for the synthesis of alkynyl C-glycosides was depicted.
8 citations
TL;DR: In this paper, the title compounds were conveniently synthesized by a phase transfer catalyzed approach in two steps and one pot using the rhamnopyranosyl chloride as key intermediate.
3 citations
Patent•
17 May 2017
TL;DR: In this paper, an oligosaccharide synthesizing method is characterized in that full-benzyl protection propargyl alcohol glycoside is utilized as a glycosyl donor, 6-site glyco-intermediate or glyco with a -Tr protecting group is used as an acceptor, and the glycoyl donor and the acceptor are dissolved in an organic solvent according to a mole ratio of (1 to 6mmol) to 1mmol to (0.1 to 1mol) for catalysis of ferric salt.
Abstract: The invention discloses an oligosaccharide synthesizing method which is characterized in that full-benzyl protection propargyl alcohol glycoside is utilized as a glycosyl donor, 6-site glycosyl intermediate or glycosyl with a -Tr protecting group is utilized as a glycosyl acceptor, and the glycosyl donor and the glycosyl acceptor are dissolved in an organic solvent according to a mole ratio of (1 to 6mmol) to 1mmol to (0.1 to 1mmol) to perform glycosylation reaction under the catalysis of ferric salt. Compared with the prior art, the oligosaccharide synthesizing method achieves the purpose that the glycosyl donor directly perform glycosylation reaction with the 6-site glycosyl intermediate with the -Tr protecting group, oligosaccharide is synthesized through a one-pot method in high yield, a reaction route is shortened, operation steps are simplified, production cost is reduced, and heavy metal ion pollution is effectively avoided. In addition, the oligosaccharide synthesizing method has the advantages of being green, environment-friendly and suitable for industrial production and having larger technological innovation and good application prospect.