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 …

Guidelines for O-Glycoside Formation from First Principles

PR Andreana, D Crich - 2021 - ACS Publications
Guidelines for O-Glycoside Formation from First Principles | ACS Central Science ACS ACS
Publications C&EN CAS Find my institution Log In ACS Central Science ACS Publications …

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 …

Design of α‐selective glycopyranosyl donors relying on remote anchimeric assistance

BS Komarova, YE Tsvetkov… - The Chemical Record, 2016 - Wiley Online Library
Oligosaccharides have a variety of versatile biological effects, but unlike peptides and
oligonucleotides, investigation of the roles of oligosaccharides is not easy. Since …

Theoretical investigation of solvent effects on glycosylation reactions: stereoselectivity controlled by preferential conformations of the intermediate oxacarbenium …

H Satoh, HS Hansen, S Manabe… - Journal of chemical …, 2010 - ACS Publications
The mechanism of solvent effects on the stereoselectivity of glycosylation reactions is
investigated using quantum-mechanical (QM) calculations and molecular dynamics (MD) …

The intriguing dual-directing effect of 2-cyanobenzyl ether for a highly stereospecific glycosylation reaction

K Le Mai Hoang, XW Liu - Nature Communications, 2014 - nature.com
The diverse presence as well as their very specific bio-responses of glycoconjugates found
in all living species requires scientists to synthesize the precise structure of these complex …

Hydrogen Bond Mediated Aglycone Delivery: Synthesis of Linear and Branched α‐Glucans

JP Yasomanee, AV Demchenko - … Chemie International Edition, 2014 - Wiley Online Library
A Hydrogen bond mediated aglycone delivery (HAD) method was applied to the synthesis of
α‐glucans, which are abundant in nature, but as targets represent a notable challenge to …

Modulating glycosylation with exogenous nucleophiles: an overview

SK Mulani, WC Hung, AB Ingle, KS Shiau… - Organic & Biomolecular …, 2014 - pubs.rsc.org
The major challenge in carbohydrate synthesis is stereochemical control of glycosidic bond
formation. Different glycosylation methods have been developed that are based on the …

Neighboring‐Group Participation by C‐2 Ether Functions in Glycosylations Directed by Nitrile Solvents

CS Chao, CY Lin, S Mulani, WC Hung… - … –A European Journal, 2011 - Wiley Online Library
Ether‐protecting functions at C‐2 hydroxy groups have been found to play participating roles
in glycosylations when the reactions are conducted in nitrile solvent mixtures. The …