Creating glycoside diversity through stereoselective carboboration of glycals DOI Creative Commons

Zhenpeng Shen,

Yue Yu, Donghai Wu

et al.

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

Published: Nov. 23, 2024

Site-specific modification of glycosides to enhance or alter the physiological properties parent molecule has become a highly attractive strategy in drug development. However, creating glycoside building blocks with multiple diversifiable positions from readily available sugar precursors remains challenging task. Herein, we present regio- and stereoselective nickel-catalyzed carboboration glycals, which offers platform for generating diversity diverse C1 C2 potential. Specially, integration modifiable boronate group at position markedly amplifies versatility this approach, furnishing universal method swiftly rare sugars C2-site modifications through expedited downstream transformations. This demonstrates broad substrate scope tolerates various functional groups complex natural molecular architectures. Moreover, illustrate synthetic potential synthesis array analogs both products pharmaceuticals. Creating authors

Language: Английский

Switchable and Stereospecific C-Glycosylation Strategy via Formal Functional Group Deletion DOI
Xiaoshen Ma,

Stephen J. Sujansky

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

Published: April 9, 2025

Carbohydrates constitute an important class of biologically relevant natural products. Among the synthetic glycomimetics, C-glycosides are particularly interesting due to their chemical and metabolic stability toward acidic enzymatic hydrolysis at anomeric position. The stereochemical outcomes traditional methodologies access rely heavily on substrate control. Herein, we report a novel strategy diverse with precise control position via formal functional group deletion, where both α- β-anomers furanoses pyranoses can be obtained as single stereoisomers. Additionally, broad scope heterocyclic this further illustrates its potential for empowering future application in biology research drug discovery.

Language: Английский

Citations

0
Radical dehydroxylative C-glycosylation of 1-hydroxycarbohydrates enabled by photoredox catalysis DOI Creative Commons
Wenyan Shi,

Xingxiu Yan,

Wuyin Wang

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Language: Английский

Citations

0
Stereoselective synthesis of C-glycosides from glycals and organotrifluoroborate salts DOI

Karwan Abdulmajed Othman,

Yimin Xiang,

Yue Wang

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Harnessing aryltrifluoroborates' stability and reactivity, we developed a Pd-catalyzed stereoselective C-glycosylation under ambient conditions, yielding diverse C-aryl glycosides with exclusive α-stereoselectivity compatibility hydroxyl, amide, amine groups. This method enables functionalization to produce unprotected C-pyranosides, 2,3-dideoxy 2,3-epoxy sugars, late-stage of natural products drugs.

Language: Английский

Citations

0
ZnI2-Mediated cis-Glycosylations of Various Constrained Glycosyl Donors: Recent Advances in cis-Selective Glycosylations DOI Creative Commons
Akihiro Ishiwata,

Xuemei Zhong,

Katsunori Tanaka

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(19), P. 4710 - 4710

Published: Oct. 4, 2024

An efficient and versatile glycosylation methodology is crucial for the systematic synthesis of oligosaccharides glycoconjugates. A direct intermolecular an indirect intramolecular have been developed, former can be applied to medium-to-long-chain glycans like that nucleotides peptides. The development a generally applicable approach stereoselective construction glycosidic bonds remains major challenge, especially 1,2-

Language: Английский

Citations

0
Creating glycoside diversity through stereoselective carboboration of glycals DOI Creative Commons

Zhenpeng Shen,

Yue Yu, Donghai Wu

et al.

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

Published: Nov. 23, 2024

Site-specific modification of glycosides to enhance or alter the physiological properties parent molecule has become a highly attractive strategy in drug development. However, creating glycoside building blocks with multiple diversifiable positions from readily available sugar precursors remains challenging task. Herein, we present regio- and stereoselective nickel-catalyzed carboboration glycals, which offers platform for generating diversity diverse C1 C2 potential. Specially, integration modifiable boronate group at position markedly amplifies versatility this approach, furnishing universal method swiftly rare sugars C2-site modifications through expedited downstream transformations. This demonstrates broad substrate scope tolerates various functional groups complex natural molecular architectures. Moreover, illustrate synthetic potential synthesis array analogs both products pharmaceuticals. Creating authors

Language: Английский

Citations

0