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 …
glycosides, oligosaccharides and glycoconjugates. Glycan complexity, determined by …
The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1–SN2 Interface
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 …
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 …
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 …
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 …
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 …
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 …
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 …
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 …
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
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 …
tuberculosis (Mtb) is the causative agent for tuberculosis, a disease with high mortality …