The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1–SN2 Interface

PO Adero, H Amarasekara, P Wen, L Bohé… - Chemical …, 2018 - ACS Publications
A critical review of the state-of-the-art evidence in support of the mechanisms of
glycosylation reactions is provided. Factors affecting the stability of putative oxocarbenium …

Mechanisms of glycosylation reactions studied by low-temperature nuclear magnetic resonance

TG Frihed, M Bols, CM Pedersen - Chemical reviews, 2015 - ACS Publications
Synthesis of oligosaccharides has, for the past couple of decades, been greatly improved by
new methods and the ongoing development of new technologies, such as automation in …

The influence of acceptor nucleophilicity on the glycosylation reaction mechanism

S Van der Vorm, T Hansen, HS Overkleeft… - Chemical …, 2017 - pubs.rsc.org
A set of model nucleophiles of gradually changing nucleophilicity is used to probe the
glycosylation reaction mechanism. Glycosylations of ethanol-based acceptors, bearing …

Automated quantification of hydroxyl reactivities: Prediction of glycosylation reactions

CW Chang, MH Lin, CK Chan, KY Su… - Angewandte Chemie …, 2021 - Wiley Online Library
The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable.
We have developed a database of acceptor nucleophilic constants (Aka) to quantify the …

Defining the SN1 Side of Glycosylation Reactions: Stereoselectivity of Glycopyranosyl Cations

T Hansen, L Lebedel, WA Remmerswaal… - ACS central …, 2019 - ACS Publications
The broad application of well-defined synthetic oligosaccharides in glycobiology and
glycobiotechnology is largely hampered by the lack of sufficient amounts of synthetic …

A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art

L Bohé, D Crich - Carbohydrate research, 2015 - Elsevier
An overview of recent advances in glycosylation with particular emphasis on mechanism is
presented. The mounting evidence for both the existence of glycosyl oxocarbenium ions as …

Recent Advances in Stereoselective Chemical O-Glycosylation Reactions

MM Mukherjee, R Ghosh, JA Hanover - Frontiers in Molecular …, 2022 - frontiersin.org
Carbohydrates involving glycoconjugates play a pivotal role in many life processes. Better
understanding toward glycobiological events including the structure–function relationship of …

Highly Stereoselective β‐Mannopyranosylation via the 1‐α‐Glycosyloxy‐isochromenylium‐4‐gold (I) Intermediates

Y Zhu, B Yu - Chemistry–A European Journal, 2015 - Wiley Online Library
While the gold (I)‐catalyzed glycosylation reaction with 4, 6‐O‐benzylidene tethered
mannosyl ortho‐alkynylbenzoates as donors falls squarely into the category of the Crich …

Synthesis of l-Hexoses

TG Frihed, M Bols, CM Pedersen - Chemical reviews, 2015 - ACS Publications
In this review we focus on the synthesis of compounds that are the rare antipodes of
common hexoses. Therefore, we only cover L-aldohexoses, 2-keto-L-hexoses, and 6-deoxy …

Probing the Influence of a 4,6-O-Acetal on the Reactivity of Galactopyranosyl Donors: Verification of the Disarming Influence of the trans–gauche Conformation of C5 …

M Moumé-Pymbock, T Furukawa… - Journal of the …, 2013 - ACS Publications
The effect of a 4, 6-O-alkylidene acetal on the rate of acid-catalyzed hydrolysis of methyl
galactopyranosides and of spontaneous hydrolysis of 2, 4-dinitrophenyl galactopyranosides …