Mechanisms of stereodirecting participation and ester migration from near and far in glycosylation and related reactions

AA Hettikankanamalage, R Lassfolk, FS Ekholm… - Chemical …, 2020 - ACS Publications
This review is the counterpart of a 2018 Chemical Reviews article (Adero, PO; Amarasekara,
H.; Wen, P.; Bohé, L.; Crich, D. Chem. Rev. 2018, 118, 8242–8284) that examined the …

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 …

Mechanistic Insights into the Gold(I)-Catalyzed Activation of Glycosyl ortho-Alkynylbenzoates for Glycosidation

Y Tang, J Li, Y Zhu, Y Li, B Yu - Journal of the American Chemical …, 2013 - ACS Publications
Anomerization, which involves cleavage and formation of the anomeric C–O bond, is of
fundamental importance in the carbohydrate chemistry. Herein, the unexpected gold (I) …

Chiral reagents in glycosylation and modification of carbohydrates

HY Wang, SA Blaszczyk, G **ao, W Tang - Chemical Society Reviews, 2018 - pubs.rsc.org
Carbohydrates play a significant role in numerous biological events, and the chemical
synthesis of carbohydrates is vital for further studies to understand their various biological …

Advances in Stereoselective 1,2‐cis Glycosylation using C‐2 Auxiliaries

RA Mensink, TJ Boltje - Chemistry–A European Journal, 2017 - Wiley Online Library
The control of stereoselectivity in a glycosylation reaction remains one of the most
challenging aspects of oligosaccharide synthesis. Especially the synthesis of 1, 2‐cis …

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 …

Stereoselective assembly of complex oligosaccharides using anomeric sulfonium ions as glycosyl donors

T Fang, KF Mo, GJ Boons - Journal of the American Chemical …, 2012 - ACS Publications
The development of selectively protected monosaccharide building blocks that can reliably
be glycosylated with a wide variety of acceptors is expected to make oligosaccharide …

Cation clock reactions for the determination of relative reaction kinetics in glycosylation reactions: Applications to gluco-and mannopyranosyl sulfoxide and …

PO Adero, T Furukawa, M Huang… - Journal of the …, 2015 - ACS Publications
The development of a cation clock method based on the intramolecular Sakurai reaction for
probing the concentration dependence of the nucleophile in glycosylation reactions is …

Preactivation: an alternative strategy in stereoselective glycosylation and oligosaccharide synthesis

L Yang, Q Qin, XS Ye - Asian Journal of Organic Chemistry, 2013 - Wiley Online Library
The multifaceted biological importance of carbohydrates has made them very popular
targets in modern synthetic chemistry. Great progress has been made in stereoselective …