Glycosylation with sulfoxide-based glycosyl donors

P Wu, J Zeng, L Meng, Q Wan - Chemical Communications, 2024 - pubs.rsc.org
Sulfoxides have emerged as pivotal constituents in modern carbohydrate chemistry. As
anomeric leaving groups, sulfinyl moieties may occupy positions directly at the anomeric …

Anomeric Triflates versus Dioxanium Ions: Different Product-Forming Intermediates from 3-Acyl Benzylidene Mannosyl and Glucosyl Donors

WA Remmerswaal, H Elferink… - The Journal of …, 2024 - ACS Publications
Minimal structural differences in the structure of glycosyl donors can have a tremendous
impact on their reactivity and the stereochemical outcome of their glycosylation reactions …

[HTML][HTML] Characterization of elusive rhamnosyl dioxanium ions and their application in complex oligosaccharide synthesis

PH Moons, F Ter Braak, FFJ de Kleijne… - Nature …, 2024 - nature.com
Attaining complete anomeric control is still one of the biggest challenges in carbohydrate
chemistry. Glycosyl cations such as oxocarbenium and dioxanium ions are key …

[HTML][HTML] Mechanistic insight into benzylidene-directed glycosylation reactions using cryogenic infrared spectroscopy

CW Chang, K Greis, GRD Prabhu, D Wehner… - Nature …, 2024 - nature.com
Abstract The stereoselective formation of 1, 2-cis glycosidic linkages is challenging. The
currently most widely used strategy for their installation uses 4, 6-O-benzylidene-protected …

The influence of acceptor acidity on hydrogen bond mediated aglycone delivery (HAD) through the picoloyl protecting group

WA Remmerswaal, D Hoogers… - European Journal of …, 2024 - Wiley Online Library
The outcome of glycosylation reactions heavily relies on the specific protecting group
patterns employed on both the donor and acceptor molecules. The picoloyl (Pico) protecting …

Development of a Cryogenic Flow Reactor to Optimize Glycosylation Reactions Based on the Active Donor Intermediate

VA Jones, GQ Bennett, JR Pierre-Louis… - … Process Research & …, 2024 - ACS Publications
The development of a continuous flow reactor for stereospecific glycosylation reactions with
deoxy sugars is described. This apparatus that permits optimizing the selectivity of …

Anomeric Triflates vs Dioxanium ions: Different Product-Forming Intermediates from 1-Thiophenyl-2-O-Benzyl-3-O-Benzoyl-4, 6-O-Benzylidene-Mannose and Glucose

W Remmerswaal, H Elferink, K Houthuijs, T Hansen… - 2023 - chemrxiv.org
Minimal structural differences in the structure of glycosyl donors can have a tremendous
impact on their reactivity and the stereochemical outcome of their glycosylation reactions. It …

Origins of Temperature‐Dependent Anomeric Selectivity in Glycosylations with an L–Idose Thioglycoside

NW See, RB Roseli, N Wimmer, TT Le… - … A European Journal, 2024 - Wiley Online Library
L–Idose thioglycosides are useful glycosyl donors for the construction of glycosaminoglycan
oligosaccharides. When activated with NIS and catalytic TMSOTf in the presence of …

Role of ion pairs in model glycosylation reactions of permethylated glucosyl and xylosyl triflates

H Sakai, S Tsushida, T Hosoya, H Miyafuji - Carbohydrate Research, 2024 - Elsevier
Elucidating the molecular mechanisms of chemical O-glycosylation remains a significant
challenge in glycochemistry. This study examines the mechanism of the nucleophilic …

[PDF][PDF] Computational and experimental studies of reacti e intermediates in gl cos lation reactions

W Remmerswaal - scholarlypublications …
Carbohydrates, along with their derivatives known as glycoconjugates, represent the largest
and most varied group of biological molecules found in nature, being present in all life forms …