Visible-Light-Promoted Direct Desulfurization of Glycosyl Thiols to Access of C-Glycosides DOI
Xiaofeng Ma,

Demeng Xie,

Wei Zeng

et al.

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: July 3, 2024

Abstract C-Glycosides are essential for the study of biological processes and development carbohydrates-based drugs. Despite tremendous hurdles, glycochemists have often fantasized 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 in two or three from native sugars activated situ by pentafluoropyridine. The benefits this procedure include high stereoselectivity, broad substrates scope, easily handle. Mechanistic studies indicated produced tetrafluoropyridyl S-glycosides formed key EDA complexes Hantzsch ester (for C-alkyl glycosides) Et3N coumarin C-glycosides), upon irradiation visible light, triggered cascade process access smoothly.

Language: Английский

(1R)-2,3,4,6-Tetra-O-benzyl-1-C-allyl-1-deoxy-1-C-(2-thiazolyl)-D-galactopyranose DOI Creative Commons
Clark Ferrari,

Alessandro Dondoni,

Alberto Marra

et al.

Molbank, Journal Year: 2025, Volume and Issue: 2025(1), P. M1949 - M1949

Published: Jan. 8, 2025

We have previously reported that thiazolylketol acetates, synthesized by the addition of 2-lithiothiazole to sugar lactones followed acetylation, are efficient glycosyl donors affording O-, N-, P-, and C-glycosides. After first example C-glycosidation recently described us, we report here on unexpected outcome reaction a acetate with allyltrimethylsilane in presence trimethylsilyl triflate. The obtained intermediate, an intramolecular N-thiazolium salt, could be stereoselectively converted into desired allyl C-thiazolylketoside.

Language: Английский

Citations

0
Visible-light-promoted direct desulfurization of glycosyl thiols to access C-glycosides DOI Creative Commons

Demeng Xie,

Wei Zeng, Jian Yang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Oct. 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

Language: Английский

Citations

2
Thiazolylketol Acetates as Glycosyl Donors: Stereoselective Synthesis of a C-Ketoside DOI Creative Commons
Clark Ferrari,

Alessandro Dondoni,

Alberto Marra

et al.

Molbank, Journal Year: 2024, Volume and Issue: 2024(3), P. M1883 - M1883

Published: Sept. 23, 2024

We have already proven that thiazolylketol acetates, synthetised by addition of 2-lithiothiazole to sugar lactones followed acetylation, are efficient glycosyl donors in the presence O-, N-, and P-nucleophiles. describe here their first use C-glycosidation using trimetylsilyl cyanide as acceptor order prepare, after thiazole-to-formyl unmasking reduction, corresponding C-ketosides.

Language: Английский

Citations

1
Visible-Light-Promoted Direct Desulfurization of Glycosyl Thiols to Access of C-Glycosides DOI
Xiaofeng Ma,

Demeng Xie,

Wei Zeng

et al.

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: July 3, 2024

Abstract C-Glycosides are essential for the study of biological processes and development carbohydrates-based drugs. Despite tremendous hurdles, glycochemists have often fantasized 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 in two or three from native sugars activated situ by pentafluoropyridine. The benefits this procedure include high stereoselectivity, broad substrates scope, easily handle. Mechanistic studies indicated produced tetrafluoropyridyl S-glycosides formed key EDA complexes Hantzsch ester (for C-alkyl glycosides) Et3N coumarin C-glycosides), upon irradiation visible light, triggered cascade process access smoothly.

Language: Английский

Citations

0