AI Article Synopsis
- The study demonstrates a new Ni-catalyzed method for stereoselective N-glycosylation of glycals, which is made possible by using an in situ generated nickel hydride to facilitate the reaction.
- This approach allows for the creation of both α- and β-N-glycosides through either kinetic or thermodynamic pathways, providing flexibility in product formation.
- The method is noted for its simplicity, versatility, and high selectivity, making it a valuable tool for the synthesis of N-glycosides in organic chemistry.
Article Abstract
Herein, we describe a stereoselective Ni-catalyzed N-glycosylation of glycals. The reaction is enabled by addition of an in situ generated nickel hydride across an olefin prior to C-N bond-formation. Stereodivergence can be accomplished on kinetic or thermodynamic grounds, thus giving access to either α- or β-N-glycosides with equal ease. The protocol is distinguished by its operational simplicity, generality and exquisite selectivity, thus offering a new gateway to expedite the synthesis of N-glycosides.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.202403822 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Ni-Catalyzed Stereodivergent Synthesis of N-Glycosides.
Chemistry
November 2024
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
Article Synopsis
- The study demonstrates a new Ni-catalyzed method for stereoselective N-glycosylation of glycals, which is made possible by using an in situ generated nickel hydride to facilitate the reaction.
- This approach allows for the creation of both α- and β-N-glycosides through either kinetic or thermodynamic pathways, providing flexibility in product formation.
- The method is noted for its simplicity, versatility, and high selectivity, making it a valuable tool for the synthesis of N-glycosides in organic chemistry.
Cobalt-Catalyzed Highly α-Stereoselective Glycosylation of Glycals.
Org Lett
December 2024
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, Hangzhou, 311121, P. R. China.
Following the satisfactory catalytic performance of cobalt in the -glycosylation of glycals, further study of cobalt's application values was performed under mild conditions, leading to a range of highly α-stereoselective 2,3-unsaturated , , and glycosides. The synthetic potential of the developed protocol was underscored by the late-stage functionalization of pharmaceutically relevant molecules including the canagliflozin derivative (a potential candidate for treating type 2 diabetes and alleviating pathological aging). Furthermore, control experiments were conducted to elucidate a reasonable mechanism and rule out the pathway involving the configuration conversion between and anomers.
View Article and Find Full Text PDF-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity.
Beilstein J Org Chem
November 2024
Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany.
Indigo, indirubin, and isoindigo derivatives have been used for centuries as pigments. Since the 1990s, a new aspect of the chemistry of this type of compounds is their activity against various types of cancer. -Glycosides of indigo, indirubin, and isoindigo, blue, red, and yellow sugars, turned out to be of special interest because of their high cancerostatic activity and structural novelty.
View Article and Find Full Text PDFDevelopment of ketalized unsaturated saccharides as multifunctional cysteine-targeting covalent warheads.
Commun Chem
September 2024
State Key Laboratory of Drug Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai, 201203, China.
Multi-functional cysteine-targeting covalent warheads possess significant therapeutic potential in medicinal chemistry and chemical biology. Herein, we present novel unsaturated and asymmetric ketone (oxazolinosene) scaffolds that selectively conjugate cysteine residues of peptides and bovine serum albumin under normal physiological conditions. This unsaturated saccharide depletes GSH in NCI-H1299 cells, leading to anti-tumor effects in vitro.
View Article and Find Full Text PDFPalladium-Catalyzed Regio- and Stereoselective Glycosylation of Azole Heterocycles Enables Access to Diverse Heterocyclic -Glycosides.
Org Lett
August 2024
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, P. R. China.
An efficient and practical glycosylation platform for synthesizing -glycosides by leveraging palladium catalysis is disclosed. This approach enables facile access to diverse heterocyclic -glycosides with excellent regio- and stereoselectivities and high site selectivity of multiple N atoms. The reaction exhibits a broad substrate scope (65 examples), high functional group tolerance, and easy scalability.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!