Concise synthesis of 3-C-glycosyl isocoumarins and 2- glycosyl-4H-chromen-4-ones DOI

Deng-Yin Liu,

Yu-Jun Ruan,

Xiaoli Wang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(75), P. 10390 - 10393

Published: Jan. 1, 2024

A new Ru-catalyzed C-H activation/cyclization reaction for the synthesis of 3-

Language: Английский

Photoredox-Catalyzed Synthesis of C-Benzoselenazolyl/Benzothiazolyl Glycosides from 2-Isocyanoaryl Selenoethers/Thioethers and Glycosyl Bromides DOI

Yi Jiao,

Xiaoran Shi,

Lei Ju

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(1), P. 390 - 395

Published: Jan. 2, 2024

Molecules containing heteroatoms, such as Se and S, play an indispensable role in the discovery design of pharmaceuticals, whereas has been less studied. Here, we described a photoredox strategy to synthesize C-benzoselenazolyl (Bs) glycosides from 2-isocyanoaryl selenoethers glycosyl bromides. This reaction was carried out under mild conditions with high efficiency. C-Benzothiazolyl (Bt) could also be synthesized thioethers using this strategy. method can access novel seleno/thiosugars, which will benefit Se/S-containing drug discovery.

Language: Английский

Citations

9
Photocatalytic cyclization of 3-(2-isocyanophenyl)quinazolin-4(3H)-ones for the construction of quinoxalino[2,1-b]quinazolinones DOI

Xian Wu,

Ling-Li Liu,

Chengli Xiang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(18), P. 2556 - 2559

Published: Jan. 1, 2024

3-(2-Isocyanophenyl)quinazolin-4(3 H )-ones were designed and synthesized as new building units for the construction of novel quinoxalino[2,1- b ]quinazolinones under mild, photocatalytic metal-free conditions.

Language: Английский

Citations

5
Pd-Catalyzed Stereospecific Glycosyl Cross-Coupling of Reversed Anomeric Stannanes for Modular Synthesis of Nonclassical C-Glycosides DOI Creative Commons
Cheng Guo-qiang, Bo Yang, Zhi Yang

et al.

Precision Chemistry, Journal Year: 2024, Volume and Issue: 2(11), P. 587 - 599

Published: July 21, 2024

Nonclassical C-glycosides, distinguished by their unique glycosidic bond connection mode, represent a promising avenue for the development of carbohydrate-based drugs. However, accessibility nonclassical C-glycosides hinders broader investigations into structural features and modes action. Herein, we present first example Pd-catalyzed stereospecific glycosylation anomeric stannanes with aryl or vinyl halides. This method furnishes desired in good to excellent yields, while allowing exclusive control configuration. Of significant note is demonstration generality practicality this C-glycosylation approach across more than 50 examples, encompassing various protected unprotected saccharides, deoxy sugars, oligopeptides, complex molecules. Furthermore, biological evaluation indicates that modifications drug molecules can positively impact activity. Additionally, extensive computational studies are conducted elucidate rationale behind differences reaction reactivity, unveiling transmetalation transition state containing silver (Ag) within six-membered ring. Given its remarkable controllability, predictability, consistently high chemical selectivity stereospecificity regarding carbon Z/E configuration, outlined study offers solution longstanding challenge accessing stereocontrol.

Language: Английский

Citations

4
Photoredox-Mediated Radical Addition/Cyclization To Construct Benzannulated 6,5-Spiroketal Glycosides DOI
Chen Li, Shouyun Yu

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 30, 2025

We herein present a green and mild photoredox strategy for constructing framework of benzannulated 6,5-spiroketal glycosides. This method employs various O-arylacetylene glycosides aryl ketone acids as the starting materials, facilitating rapid straightforward synthesis with up to 92% yields under catalytic conditions. efficient approach has potential significantly enhance molecular library carbohydrate-based pharmaceuticals.

Language: Английский

Citations

0
Photoredox Radical Cyclization of o-Vinylaryl Isocyanides and Aryldiazonium Tetrafluoroborates for the Synthesis of 2,4-Disubstituted Quinolines DOI
Min Gao, Chuan Ding, Peng‐Fei Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 23, 2025

Quinolines, a significant part of nitrogen-containing heterocycles, are widely found in functional compounds. Herin, photochemical radical cyclization reaction o-vinylaryl isocyanides and aryldiazonium tetrafluoroborates, has been reported to build 2,4-diaryl quinolines. Readily accessible aryl diazonium salts were utilized as precursors at room temperature. This approach allowed good group tolerance substrate applicability.

Language: Английский

Citations

0
Recent Advances in Strategies for Halide Atom Transfer (XAT) and Their Applications DOI

Yifeng Jiang,

Yanli Yin, Zhiyong Jiang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(6), P. 1733 - 1733

Published: Jan. 1, 2024

Language: Английский

Citations

2
Photoredox-Catalyzed C-Indolyl/Quinolyl Glycosylation from 2-Styrylisocyanides and Glycosyl Bromides DOI

Yi Jiao,

Xiaoran Shi,

Yiqiang Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(38), P. 8149 - 8153

Published: Sept. 16, 2024

Indole and quinoline structures are present in numerous biologically active molecules, making the synthesis of their glycosylation products a subject extensive research interest drug development. Here, we report photoredox strategy for

Language: Английский

Citations

2
“Boomerang” Strategy in Carbohydrate Chemistry: Diastereoselective Synthesis of C-Glycosylated Benzothiazoles from ortho-Isocyanophenyl Thioglycosides DOI

Li‐Yan Hu,

Shen‐Yuan Zhang,

Li Zhu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 26(1), P. 215 - 220

Published: Dec. 20, 2023

This paper reveals a novel "boomerang" strategy in the expedient and diastereoselective synthesis of C-nucleoside analogues. Bench-stable ortho-isocyanophenyl thioglycosides can be converted to glycosyl radicals through rapid efficient C–S bond homolysis when they are irradiated by visible light. The subsequently trapped corresponding leaving group or other radical acceptors provide diverse analogues under mild conditions.

Language: Английский

Citations

5
Stereoselective Synthesis of C-Aryl-α-Glycosides by Reductive C(sp2)–C(sp3) Cross-Coupling Reaction DOI

Noyuri Kudo,

Suzuka Chiba,

Kazuteru Usui

et al.

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: June 25, 2024

Abstract C-Aryl glycosides have attracted considerable interest as biologically active natural products and O-aryl glycoside mimetics in drug discovery. Here, we describe a straightforward synthesis of C-aryl by photoredox/Ni dual-catalyzed reductive cross-coupling between glycosyl bromides aryl bromides. This methodology enables highly α-stereoselective glucosides, galactosides, mannosides.

Language: Английский

Citations

0
Concise synthesis of 3-C-glycosyl isocoumarins and 2- glycosyl-4H-chromen-4-ones DOI

Deng-Yin Liu,

Yu-Jun Ruan,

Xiaoli Wang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(75), P. 10390 - 10393

Published: Jan. 1, 2024

A new Ru-catalyzed C-H activation/cyclization reaction for the synthesis of 3-

Language: Английский

Citations

0