Advances in glycoside and oligosaccharide synthesis

CJ Crawford, PH Seeberger - Chemical Society Reviews, 2023 - pubs.rsc.org
The structural complexity of glycans poses a serious challenge in the chemical synthesis of
glycosides, oligosaccharides and glycoconjugates. Glycan complexity, determined by …

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 …

Acceptor reactivity in glycosylation reactions

S Van Der Vorm, T Hansen, JMA Van Hengst… - Chemical Society …, 2019 - pubs.rsc.org
The outcome of a glycosylation reaction critically depends on the reactivity of all reaction
partners involved: the donor glycoside (the electrophile), the activator (that generally …

Borinic acid catalyzed stereo-and regioselective couplings of glycosyl methanesulfonates

KA D'Angelo, MS Taylor - Journal of the American Chemical …, 2016 - ACS Publications
In the presence of a diarylborinic acid catalyst, glycosyl methanesulfonates engage in regio-
and stereoselective couplings with partially protected pyranoside and furanoside acceptors …

Stereospecific furanosylations catalyzed by bis-thiourea hydrogen-bond donors

AB Mayfield, JB Metternich, AH Trotta… - Journal of the …, 2020 - ACS Publications
We report a new method for stereoselective O-furanosylation reactions promoted by a
precisely tailored bis-thiourea hydrogen-bond-donor catalyst. Furanosyl donors outfitted with …

Regioselective and Stereospecific β‐Arabinofuranosylation by Boron‐Mediated Aglycon Delivery

K Inaba, Y Naito, M Tachibana, K Toshima… - Angewandte …, 2023 - Wiley Online Library
Regio‐and stereoselective formation of the 1, 2‐cis‐furanosidic linkage has been in great
demand for efficient synthesis of biologically active natural glycosides. In this study, we …

Twenty years of mycobacterial glycans: furanosides and beyond

TL Lowary - Accounts of chemical research, 2016 - ACS Publications
Conspectus The cell surface (or cell wall) of bacteria is coated with carbohydrate (or glycan)
structures that play a number of important roles. These include providing structural integrity …

Five Triisopropylsilyl Substituents in Ara‐β‐(1→ 2)‐Ara Disaccharide Glycosyl Donor Make Unselective Glycosylation Reaction Stereoselective

PI Abronina, NN Malysheva… - European Journal of …, 2022 - Wiley Online Library
Abstract Formation of 1, 2‐trans‐arabinofuranoside linkage in arabinans from
Mycobacterium tuberculosis using differently protected Ara‐β‐(1→ 2)‐Ara disaccharide …

The use of silyl groups in the synthesis of arabinofuranosides

PI Abronina, NM Podvalnyy, LO Kononov - Russian Chemical Bulletin, 2022 - Springer
The review considers the known strategies for the synthesis of fragments of arabinogalactan
and lipoarabinomannan, polysaccharides that are contained in the cell walls of causative …

Expedient synthesis of the heneicosasaccharyl mannose capped arabinomannan of the Mycobacterium tuberculosis cellular envelope by glycosyl carbonate donors

M Islam, GP Shinde, S Hotha - Chemical Science, 2017 - pubs.rsc.org
The global incidence of tuberculosis is increasing at an alarming rate, and Mycobacterium
tuberculosis (Mtb) is the causative agent for tuberculosis, a disease with high mortality …