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 …
Unraveling the promoter effect and the roles of counterion exchange in glycosylation reaction
CW Chang, MH Lin, TY Chiang, CH Wu, TC Lin… - Science …, 2023 - science.org
The stereoselectivity of glycosidic bond formation continues to pose a noteworthy hurdle in
synthesizing carbohydrates, primarily due to the simultaneous occurrence of SN1 and SN2 …
synthesizing carbohydrates, primarily due to the simultaneous occurrence of SN1 and SN2 …
Mechanistic insight into benzylidene-directed glycosylation reactions using cryogenic infrared spectroscopy
Abstract The stereoselective formation of 1, 2-cis glycosidic linkages is challenging. The
currently most widely used strategy for their installation uses 4, 6-O-benzylidene-protected …
currently most widely used strategy for their installation uses 4, 6-O-benzylidene-protected …
Neighboring‐Group Participation by C‐2 Acyloxy Groups: Influence of the Nucleophile and Acyl Group on the Stereochemical Outcome of Acetal Substitution …
Y Chun, WA Remmerswaal, JDC Codée… - … A European Journal, 2023 - Wiley Online Library
A single acyloxy group at C‐2 can control the outcome of nucleophilic substitution reactions
of pyran‐derived acetals, but the extent of the neighboring‐group participation depends on a …
of pyran‐derived acetals, but the extent of the neighboring‐group participation depends on a …
Influence of C-4 Axial/Equatorial Configuration and Neighboring Group/Remote Group Participation (NGP/RGP) Driven Conformational Evidence in Chemoselective …
We herein reveal the possibility of the C-4 neighboring group/remote group participation
(NGP/RGP) facilitating the stabilization of the anomeric center via dioxolenium intermediates …
(NGP/RGP) facilitating the stabilization of the anomeric center via dioxolenium intermediates …
Origins of Selectivity in Glycosylation Reactions with Saccharosamine Donors
BP Garreffi, RW Kwok, M Marianski, CS Bennett - Organic Letters, 2023 - ACS Publications
A combination of DFT calculations and experiments is used to describe how the selection of
a promoter can control the stereochemical outcome of glycosylation reactions with the deoxy …
a promoter can control the stereochemical outcome of glycosylation reactions with the deoxy …
Characterization of elusive rhamnosyl dioxanium ions and their application in complex oligosaccharide synthesis
PH Moons, F Ter Braak, FFJ de Kleijne… - Nature …, 2024 - nature.com
Attaining complete anomeric control is still one of the biggest challenges in carbohydrate
chemistry. Glycosyl cations such as oxocarbenium and dioxanium ions are key …
chemistry. Glycosyl cations such as oxocarbenium and dioxanium ions are key …
Stereodirecting Effect of Esters at the 4-Position of Galacto- and Glucopyranosyl Donors: Effect of 4-C-Methylation on Side-Chain Conformation and Donor Reactivity …
When generated in a mass spectrometer bridged bicyclic 1, 3-dioxenium ions derived from 4-
O-acylgalactopyranosyl, donors can be observed by infrared spectroscopy at cryogenic …
O-acylgalactopyranosyl, donors can be observed by infrared spectroscopy at cryogenic …
Combination of 3-O-Levulinoyl and 6-O-Trifluorobenzoyl Groups Ensures α-Selectivity in Glucosylations: Synthesis of the Oligosaccharides Related to Aspergillus fumigatus α …
BS Komarova, NS Novikova, AG Gerbst… - The Journal of …, 2023 - ACS Publications
Stereospecific α-glucosylation of primary and secondary OH-group at carbohydrate
acceptors is achieved using glucosyl N-phenyl-trifluoroacetimidate (PTFAI) donor protected …
acceptors is achieved using glucosyl N-phenyl-trifluoroacetimidate (PTFAI) donor protected …
Mechanism of C-3 Acyl Neighboring Group Participation in Mannuronic Acid Glycosyl Donors
FFJ de Kleijne, PH Moons, F Ter Braak… - Journal of the …, 2024 - ACS Publications
One of the main challenges in oligosaccharide synthesis is the stereoselective introduction
of the glycosidic bond. In order to understand and control glycosylation reactions, thorough …
of the glycosidic bond. In order to understand and control glycosylation reactions, thorough …