Organic Letters, Год журнала: 2024, Номер unknown
Опубликована: Дек. 23, 2024
We have developed a glycosyl radical-based synthesis of
Язык: Английский
Chemical Science, Год журнала: 2024, Номер 15(4), С. 1204 - 1236
Опубликована: Янв. 1, 2024
This review article highlights the diverse ways in which recent developments areas of photocatalysis and visible light photochemistry are impacting synthetic carbohydrate chemistry.
Язык: Английский
Процитировано
33
ACS Catalysis, Год журнала: 2024, Номер 14(15), С. 11532 - 11544
Опубликована: Июль 19, 2024
Glycosyl donor activation emerged as an enabling technology for anomeric functionalization, but aimed primarily at O-glycosylation. In contrast, we herein disclose mechanistically distinct electrochemical glycosyl bromide activations via halogen-atom transfer and C-glycosylation. The radical addition to alkenes led C-alkyl glycoside synthesis under precious metal-free reaction conditions from readily available bromides. robustness of our e-XAT strategy was further mirrored by C-aryl C-acyl glycosides assembly through nickela-electrocatalysis. Our approach provides orthogonal with expedient scope, hence representing a general method direct C-glycosides assembly.
Язык: Английский
Процитировано
6
Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(6), С. 1733 - 1733
Опубликована: Янв. 1, 2024
Язык: Английский
Процитировано
3
Science China Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Янв. 2, 2025
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Апрель 6, 2025
Aryl migration, especially 1,4-aryl is one of the most important reactions in radical rearrangement. Over past decades, migration by addition a to alkynes has become simple and efficient method difunctionalization alkynes. Radical-based aryl alkynoates been well-explored; however, propynyl ethers rarely studied. Herein, we first described propargyl ether valuable α,β-unsaturated aldehydes via photoredox Ni catalysis. This features redox-neutral conditions, readily available starting materials, broad substrate scope, good functional group compatibility, diverse transformations. Mechanistic studies suggest that this reaction proceeds through radical-involved pathway.
Язык: Английский
Процитировано
0
Carbohydrate Research, Год журнала: 2025, Номер 554, С. 109537 - 109537
Опубликована: Май 17, 2025
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Май 20, 2025
A visible light-promoted, mild, and efficient Ir(III)-catalyzed synthesis of C-nucleosides is reported, utilizing 1-bromosugar as the glycosyl radical precursor 6-azauracil nucleobase. The method exhibits high α-selectivity excellent functional group tolerance. Spectroscopic evidence shows that coupling reaction happens via initial reductive quenching Ir(III) catalyst under light. Density theory calculation reveals reason for complete α-selectivity. Finally, biologically active 6-aza pseudouridine analogues were synthesized, making process a valuable platform C-nucleosides.
Язык: Английский
Процитировано
0
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(36)
Опубликована: Июнь 5, 2024
Previous N-glycosylation approaches have predominately involved acidic conditions, facing challenges of low stereoselectivity and limited scope. Herein, we introduce a radical activation strategy that enables versatile stereoselective using readily accessible glycosyl sulfinate donors under basic conditions exhibits exceptional tolerance towards various N-aglycones containing alkyl, aryl, heteroaryl nucleobase functionalities. Preliminary mechanistic studies indicate pivotal role iodide, which orchestrates the formation from subsequent generation key intermediate, configurationally well-defined is subsequently attacked by an N-aglycone in stereospecific S
Язык: Английский
Процитировано
3
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 11909 - 11920
Опубликована: Авг. 9, 2024
Melibiosamine (Gal-α(1,6)-GlcNH2), consisting of galactose and glucosamine linked by an α(1,6)-glycosidic bond, is artificial disaccharide derivative that selectively inhibits the proliferation K562 tumor cells relative to HUC-F2 normal cells. In this study, we employed a linkage-editing strategy synthesize CH2- CHF-linked melibiosamine analogs through chemo- stereoselective hydrogenation fluorovinyl-C-glycoside. (R)-CHF-Melibiosamine exhibited more potent antiproliferative activity than O-linked melibiosamine, while (S)-CHF-melibiosamine was less potent.
Язык: Английский
Процитировано
3
Nature Communications, Год журнала: 2024, Номер 15(1)
Опубликована: Окт. 24, 2024
C-Glycosides are essential for the study of biological processes and development carbohydrate-based drugs. Despite tremendous hurdles, glycochemists have often fantasized about efficient, highly stereoselective synthesis C-glycosides with shortest steps under mild conditions. Herein, we report a desulfurative radical protocol to synthesize C-alkyl glycosides coumarin visible-light induced conditions without need an extra photocatalyst, in which stable readily available glycosyl thiols that could be obtained from native sugars activated situ by pentafluoropyridine. The benefits this procedure include high stereoselectivity, broad substrate scope, easy handling. Mechanistic studies indicate produced tetrafluoropyridyl S-glycosides form key electron donor-acceptor (EDA) complexes Hantzsch ester (for glycosides) or Et
Язык: Английский
Процитировано
2