3925514

Studies in C-glycoside synthesis: from SN2-like displacement to cross coupling

Date
August 13, 2023
Explore related products in the following collection:

C-glycosides are hydrolytically stable analogs of glycans and glycoconjugates which in some cases have improved pharmacokinetic properties compared to their O-linked counterparts. While many approaches to specific C-glycosides have been described, general methods for C-linked disaccharide production are comparatively rare. This talk describes our labs studies directed to developing methods for C-linked disaccharide synthesis, including SN2 displacement of glycosyl sulfonates with carbon nucleophiles and light-free Ni-mediated cross-coupling reactions with redox active esters. The scope and limitations of these chemistries as well as the elaboration of the resulting products into C-linked disaccharides will be discussed.

Presenter

Speaker Image for Clay Bennett
Professor, Tufts University

Related Products

Thumbnail for Exploiting Siglecs as glyco-immune checkpoints to suppress unwanted immune responses
Exploiting Siglecs as glyco-immune checkpoints to suppress unwanted immune responses
The sialic acid-binding immunoglobulin type lectins (Siglecs) are a family of co-receptors that help regulate immune cell recognition of self…
Thumbnail for Synthesis and application of m-DAP containing PG probes
Synthesis and application of m-DAP containing PG probes
The microbiome is host to trillions of commensal and pathogenic bacteria. These bacteria are recognized by peptidoglycan (PG) fragments that are shed as bacteria repair and maintain their cell wall…
Thumbnail for Advances in Carbohydrate Synthesis Lead to New Research & Therapeutic’s Opportunities in the  Glycosciences:
Advances in Carbohydrate Synthesis Lead to New Research & Therapeutic’s Opportunities in the Glycosciences:
DIVISION/COMMITTEE: [CARB] Division of Carbohydrate Chemistry & Chemical Glycobiology