Search Results - "van der Vorm, Stefan"
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Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions
Published in Nature communications (29-05-2020)“…Controlling the chemical glycosylation reaction remains the major challenge in the synthesis of oligosaccharides. Though 1,2- trans glycosidic linkages can be…”
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Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity
Published in Angewandte Chemie International Edition (02-07-2018)“…The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and…”
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Stereoselectivity of Conformationally Restricted Glucosazide Donors
Published in Journal of organic chemistry (05-05-2017)“…Glycosylations of 4,6-tethered glucosazide donors with a panel of model acceptors revealed the effect of acceptor nucleophilicity on the stereoselectivity of…”
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Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2‐Azidofuranoses, 2‐Fluorofuranoses and Methyl Furanosyl Uronates
Published in Chemistry : a European journal (23-05-2019)“…The 3D shape of glycosyl oxocarbenium ions determines their stability and reactivity and the stereochemical course of SN1 reactions taking place on these…”
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Defining the SN1 Side of Glycosylation Reactions: Stereoselectivity of Glycopyranosyl Cations
Published in ACS central science (22-05-2019)“…The broad application of well-defined synthetic oligosaccharides in glycobiology and glycobiotechnology is largely hampered by the lack of sufficient amounts…”
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Titelbild: Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity (Angew. Chem. 27/2018)
Published in Angewandte Chemie (02-07-2018)“…Die Stereoselektivität von Glykosylierungen kann ganz zentral von der Reaktivität des Akzeptor‐Glykosids (des Nukleophils in der Reaktion) abhängen. J. D…”
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Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity
Published in Angewandte Chemie (02-07-2018)“…The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and…”
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Synthesis of O‑1–O‑6 Substituted Positional Isomers of d‑Glucose–Thioether Ligands and Their Ruthenium Polypyridyl Conjugates
Published in Journal of organic chemistry (02-11-2018)“…A library of positional isomers of d-glucose (O-1–O-6) as ligands and their 11 light-active ruthenium conjugates has been synthesized. A protecting group…”
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Anomeric Triflates versus Dioxanium Ions: Different Product-Forming Intermediates from 3‑Acyl Benzylidene Mannosyl and Glucosyl Donors
Published in Journal of organic chemistry (02-02-2024)“…Minimal structural differences in the structure of glycosyl donors can have a tremendous impact on their reactivity and the stereochemical outcome of their…”
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Synthesis, Reactivity, and Stereoselectivity of 4‑Thiofuranosides
Published in Journal of organic chemistry (01-02-2019)“…Thiosugars, sugars that have their endocyclic oxygen substituted for a sulfur atom, have been used as stable bioisosteres of naturally occurring glycans…”
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Mapping the effect of configuration and protecting group pattern on glycosyl acceptor reactivity
Published in Chemical science (Cambridge) (08-02-2023)“…The reactivity of the acceptor alcohol can have a tremendous influence on the outcome of a glycosylation reaction, both in terms of yield and…”
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Cover Picture: Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity (Angew. Chem. Int. Ed. 27/2018)
Published in Angewandte Chemie International Edition (02-07-2018)“…The stereoselectivity of glycosylation … … reactions can depend critically on the reactivity of the acceptor glycoside (the nucleophile in the reaction). In…”
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Cover Feature: Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2‐Azidofuranoses, 2‐Fluorofuranoses and Methyl Furanosyl Uronates (Chem. Eur. J. 29/2019)
Published in Chemistry : a European journal (23-05-2019)“…Energy maps of the full conformational space of 5‐membered ring glycosyl oxocarbenium ions have been generated to probe the stereoelectronic effects of…”
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14
Defining the S N 1 Side of Glycosylation Reactions: Stereoselectivity of Glycopyranosyl Cations
Published in ACS central science (22-05-2019)“…The broad application of well-defined synthetic oligosaccharides in glycobiology and glycobiotechnology is largely hampered by the lack of sufficient amounts…”
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