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.

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.

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.

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

scholarly journals Diels–Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts

2018 ◽  
Vol 14 ◽  
pp. 354-363 ◽  
Author(s):  
Huangguan Chen ◽  
Jianwei Han ◽  
Limin Wang
Keyword(s):  
Cycloaddition Reaction ◽  
Catalytic Amount ◽  
Diels Alder ◽  
Diaryliodonium Salts ◽  
Wide Range

With a strategy of the formation of benzynes by using diaryliodonium salts, a cycloaddition reaction of N-arylpyrroles with benzynes was reported. A wide range of bridge-ring amines with various substituents have been synthesized in moderate to excellent yields (35–96%). Furthermore, with a catalytic amount of TsOH·H2O, these amines can be converted into the corresponding N-phenylamine derivatives easily, which are potentially useful in photosensitive dyes.

Recent Developments in Glycoside Synthesis with Glycosynthases and Thioglycoligases

2009 ◽  
Vol 62 (6) ◽  
pp. 510 ◽  
Author(s):  
Bojana Rakić ◽  
Stephen G. Withers
Keyword(s):  
Directed Evolution ◽  
High Throughput ◽  
Glycoside Hydrolase ◽  
Glycoside Synthesis ◽  
Wide Range ◽  
Recent Developments ◽  
Aryl Glycosides ◽  
High Throughput Screens

Glycosynthases are hydrolytically incompetent engineered glycosidases that catalyze the high-yielding synthesis of glycoconjugates from glycosyl fluoride donor substrates and appropriate acceptors. Glycosynthases from more than 10 glycoside hydrolase families have now been generated, allowing the synthesis of a wide range of oligosaccharides. Recent examples include glycosynthase-mediated syntheses of xylo-oligosaccharides, xyloglucans, glycolipids, and aryl glycosides. Glycosynthases have also now been generated from inverting glycosidases, increasing the range of enzyme scaffolds. Improvement of glycosynthase activity and broadening of specificity has been achieved through directed evolution approaches, and several novel high-throughput screens have been developed to allow this. Finally, metabolically stable glycoside analogues have been generated using another class of mutant glycosidases: thioglycoligases. Recent developments in all these aspects are discussed.

Copper-Catalyzed Stereoselective Synthesis of 2-Deoxygalactosides

Synlett ◽  
2020 ◽  
Vol 31 (11) ◽  
pp. 1087-1093 ◽  
Author(s):  
Jianbo Zhang ◽  
Youxian Dong ◽  
Madina Yuma ◽  
Yuling Mei ◽  
Nan Jiang ◽  
...  
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Mild Conditions ◽  
Excellent Yield ◽  
Wide Range ◽  
Reaction Proceeds ◽  
Additional Ligand

An efficient glycosylation method to synthesize 2-deoxy-O-galactosides based on a Cu(II)-catalyzed reaction without additional ligand has been developed. The glycosylation was amenable to different protected glycal donors and a wide range of acceptors including alcohols, amino acids, sugars, and phenol, and proceeds with excellent yield and high α-selectivity under mild conditions. The reaction proceeds readily on a gram scale, and its versatility is exemplified in the synthesis of oligosaccharides.

Sign in / Sign up

Export Citation Format

Share Document