Modular and Stereoselective Synthesis of C-Aryl Glycosides via Catellani Reaction

2020 ◽  
Vol 142 (35) ◽  
pp. 14864-14870 ◽  
Author(s):  
Weiwei Lv ◽  
Yanhui Chen ◽  
Si Wen ◽  
Dan Ba ◽  
Guolin Cheng
Keyword(s):  
Stereoselective Synthesis ◽  
Aryl Glycosides

Highly regioselective and stereoselective synthesis of C-Aryl glycosides via Nickel-catalyzed ortho-C-H glycosylation of 8-aminoquinoline benzamides

2021 ◽  
Author(s):  
Wei-Yu Shi ◽  
Ya-Nan Ding ◽  
Nian Zheng ◽  
Xue-Ya Gou ◽  
Zhe Zhang ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Cost Effective ◽  
Drug Candidates ◽  
Aryl Glycosides ◽  
Glycosylation Reaction

C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzed ortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows...

Regio- and Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides via Palladium Catalyzed Decarboxylative Reactions

2011 ◽  
Vol 13 (17) ◽  
pp. 4608-4611 ◽  
Author(s):  
Shaohua Xiang ◽  
Shuting Cai ◽  
Jing Zeng ◽  
Xue-Wei Liu
Keyword(s):  
Stereoselective Synthesis ◽  
Palladium Catalyzed ◽  
Aryl Glycosides

A Metal-free and β-Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides: Synthesis of 5-aza analogues of Aquayamycin

Synlett ◽  
2021 ◽  
Author(s):  
Yuling Mei ◽  
nan jiang ◽  
Yu Yang ◽  
Wan Zhang ◽  
Saifeng Qiu ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Metal Free ◽  
Wide Range ◽  
One Step ◽  
Aryl Glycosides ◽  
Aryl Glycoside

A convenient protocol for β-stereoselective synthesis of 2-deoxy-C-aryl glycosides has been developed. This reaction takes place in one step by using I2/Et3SiH to activate glycosyl acetate to generate glycosyl iodide intermediate in situ, which was captured by naphthol followed by Fries-like O- → C-glycoside rearrangement to selectively afford β-C-aryl glycoside. The approach is applicable to a wide range of naphthol modules, and its utility was demonstrated in the synthesis of 5-aza analogues of Aquayamycin.

Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts

2020 ◽  
Vol 18 (12) ◽  
pp. 2242-2251 ◽  
Author(s):  
Kumar Bhaskar Pal ◽  
Jiande Lee ◽  
Mrinmoy Das ◽  
Xue-Wei Liu
Keyword(s):  
Stereoselective Synthesis ◽  
Diaryliodonium Salts ◽  
Wide Range ◽  
Aryl Glycosides

An effective Pd(ii)-catalyzed stereoselective C-glycosylation method has been successfully manifested for the synthesis of diversely functionalized 2,3-dideoxy C-aryl glycosides starting from glycals with a wide range of diaryliodonium salts.

Ferric Chloride: An Eco-friendly Catalyst for the Stereoselective Synthesis of 2-Deoxy Aryl-O-Rhamnosides

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 2024-2029 ◽  
Author(s):  
Jianbo Zhang ◽  
Saifeng Qiu ◽  
Guosheng Sun ◽  
Zekun Ding ◽  
Heshan Chen
Keyword(s):  
Ferric Chloride ◽  
Stereoselective Synthesis ◽  
Substituted Phenols ◽  
Wide Range ◽  
Aryl Glycosides

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 (FeCl3). 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 (<30 min) in good to excellent yields (52–88%) with sole α-selectivity.

Sign in / Sign up

Export Citation Format

Share Document