Emerging Advances of the Radical Pathway Glycosylation Enabled by Bench‐Stable Glycosyl Donors: Glycosyl Sulfoxides, Glycosyl Sulfones, and Glycosyl Sulfinates

S Dubey, Z Azeem, PK Mandal - Advanced Synthesis & …, 2024 - Wiley Online Library
In synthetic carbohydrate chemistry, the modification of glycosyl radicals pathway stands as
a central area of focus. The radical‐based reactions often demonstrate remarkable …

Electrochemical Glycosylation via Halogen-Atom-Transfer for C-Glycoside Assembly

J Wu, R Purushothaman, F Kallert, SL Homölle… - ACS …, 2024 - ACS Publications
Glycosyl donor activation emerged as an enabling technology for anomeric
functionalization, but aimed primarily at O-glycosylation. In contrast, we herein disclose …

Iridium Photoredox-Catalyzed Stereoselective C-Glycosylation with Tetrafluoropyridin-4-yl Thioglycosides: A Facile Synthesis of C-α/β-Glucogallins and Their …

S Li, H Ding, R Cao, XL Zhang, J Li, X Sun, Y Li… - ACS …, 2024 - ACS Publications
We demonstrate an efficient, scalable, and stereoselective C-glycosylation with
thioglycosides possessing a unique photoactive tetrafluoropyridin-4-yl (TFPy) thio radical …

C–OH Bond Activation for Stereoselective Radical C-Glycosylation of Native Saccharides

H **e, S Wang, XZ Shu - Journal of the American Chemical …, 2024 - ACS Publications
Radical C-glycosylation presents a flexible and efficient method for synthesizing C-
glycosides. Existing methods always require multistep processes for generating anomeric …

Photocatalytic synthesis of α-ketonyl glycosyl compounds from glycosyl thiols and silyl enol ethers

L Hu, R Li, Y Liu, J Zhou, Z Sun - Organic Letters, 2024 - ACS Publications
The synthesis of C1-ketonyl glycosyl compounds featuring α-selectivity has seldom been
reported. We herein devise a glycosyl radical-based approach to facilely access …

Mechanochemical radical transformations in organic synthesis

S Sheikhaleslami, J Sperry - Chemistry–A European Journal, 2024 - Wiley Online Library
Organic synthesis has historically relied on solution‐phase, polar transformations to forge
new bonds. However, this paradigm is evolving, propelled by the rapid evolution of radical …

Visible-light-promoted direct desulfurization of glycosyl thiols to access C-glycosides

D **e, W Zeng, J Yang, X Ma - Nature Communications, 2024 - nature.com
C-Glycosides are essential for the study of biological processes and the development of
carbohydrate-based drugs. Despite the tremendous hurdles, glycochemists have often …

Site‐Selective Construction of N‐Linked Glycopeptides through Photoredox Catalysis

B Wei, P Huang, X Wang, Z Liu, F Tang… - Angewandte …, 2024 - Wiley Online Library
The glycosylation of peptides and proteins can significantly impact their intrinsic properties,
such as conformation, stability, antigenicity, and immunogenicity. Current methods for …

Exploration of Glycosyl Dithioimidocarbonates in Photoinduced Desulfurative Cross-Coupling Reactions

J Zhang, Q Liu, A Chiang, M Nitz - Organic Letters, 2024 - ACS Publications
Readily synthesized bench-stable glycosyl dithioimidocarbonates are useful C-glycoside
precursors. Under mild photochemical conditions, these glycosides undergo desulfurative …

Enantioconvergent and Site‐Selective Etherification of Carbohydrate Polyols through Chiral Copper Radical Catalysis

H Guo, D Tan, C Merten… - Angewandte Chemie …, 2024 - Wiley Online Library
Going beyond currently reported two electron transformations that formed the core backdrop
of asymmetric catalytic site‐selective carbohydrate polyol functionalizations, we herein …