Cargando…

Halogen Atom Participation in Guiding the Stereochemical Outcomes of Acetal Substitution Reactions

Acetal substitution reactions of α‐halogenated five‐ and six‐membered rings can be highly stereoselective. Erosion of stereoselectivity occurs as nucleophilicity increases, which is consistent with additions to a halogen‐stabilized oxocarbenium ion, not a three‐membered‐ring halonium ion. Computatio...

Descripción completa

Detalles Bibliográficos
Autores principales:	Demkiw, Krystyna M., Remmerswaal, Wouter A., Hansen, Thomas, van der Marel, Gijsbert A., Codée, Jeroen D. C., Woerpel, K. A.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	John Wiley and Sons Inc. 2022
Materias:	Research Articles
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9561118/ https://www.ncbi.nlm.nih.gov/pubmed/35980341 http://dx.doi.org/10.1002/anie.202209401

Ejemplares similares

Defining the S(N)1 Side of Glycosylation Reactions: Stereoselectivity of Glycopyranosyl Cations
por: Hansen, Thomas, et al.
Publicado: (2019)

Stabilization of Glucosyl Dioxolenium Ions by “Dual Participation” of the 2,2-Dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) Protection Group for 1,2-cis-Glucosylation
por: Remmerswaal, Wouter A., et al.
Publicado: (2022)

Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions
por: Hansen, Thomas, et al.
Publicado: (2020)

Mapping the effect of configuration and protecting group pattern on glycosyl acceptor reactivity
por: van Hengst, Jacob M. A., et al.
Publicado: (2023)

Solvent Effects in the Nucleophilic Substitutions of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate: Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations
por: Kendale, Joanna C., et al.
Publicado: (2014)

Reagent Controlled Stereoselective Synthesis of α-Glucans
por: Wang, Liming, et al.
Publicado: (2018)

Reagent Controlled Stereoselective Assembly of α‐(1,3)‐Glucans
por: Wang, Liming, et al.
Publicado: (2018)

Synthesis and Antibody Binding Studies of Schistosome-Derived Oligo-α-(1-2)-l-Fucosides
por: Harvey, Michael R., et al.
Publicado: (2021)

Why Does the Type of Halogen Atom Matter for the Radiosensitizing Properties of 5-Halogen Substituted 4-Thio-2′-Deoxyuridines?
por: Spisz, Paulina, et al.
Publicado: (2019)

Participation of the Halogens in Photochemical Reactions in Natural and Treated Waters
por: Yang, Yi, et al.
Publicado: (2017)

Mapping the Reactivity and Selectivity of 2-Azidofucosyl Donors for the Assembly of N-Acetylfucosamine-Containing Bacterial Oligosaccharides
por: Hagen, Bas, et al.
Publicado: (2017)

Stereoselectivity of Conformationally Restricted Glucosazide Donors
por: van der Vorm, Stefan, et al.
Publicado: (2017)

Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides
por: Wang, Liming, et al.
Publicado: (2020)

Assembly of a Library of Pel-Oligosaccharides Featuring α-Glucosamine and α-Galactosamine Linkages
por: Zhang, Yongzhen, et al.
Publicado: (2022)

The stereochemical course of 2-methylisoborneol biosynthesis
por: Gu, Binbin, et al.
Publicado: (2022)

An Orthogonally Protected Cyclitol for the Construction of Nigerose- and Dextran-Mimetic Cyclophellitols
por: Ofman, Tim P., et al.
Publicado: (2021)

How Lewis Acids Catalyze Ring-Openings of Cyclohexene Oxide
por: Hansen, Thomas, et al.
Publicado: (2021)

Stereochemical outcomes of C–F activation reactions of benzyl fluoride
por: Keddie, Neil S, et al.
Publicado: (2018)

Synthetic Teichoic Acid Conjugate Vaccine against Nosocomial Gram-Positive Bacteria
por: Laverde, Diana, et al.
Publicado: (2014)

The influence of acceptor nucleophilicity on the glycosylation reaction mechanism
por: van der Vorm, S., et al.
Publicado: (2017)

Mechanochemical halogenation of unsymmetrically substituted azobenzenes
por: Barišić, Dajana, et al.
Publicado: (2022)

An introduction to stereochemical restraints
por: Evans, Philip R.
Publicado: (2007)

Cyanopivaloyl Ester in the Automated Solid-Phase Synthesis of Oligorhamnans
por: Geert Volbeda, Anne, et al.
Publicado: (2017)

Photo‐Induced Halogen‐Atom Transfer: Generation of Halide Radicals for Selective Hydrohalogenation Reactions
por: Geniller, Lilian, et al.
Publicado: (2022)

Studying the Possibilities of Using 2-Halogen-Substituted Acetamides As Acyl Donors in Penicillin Acylase-Catalyzed Reactions
por: Panin, N. V., et al.
Publicado: (2019)

Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit
por: Hagen, Bas, et al.
Publicado: (2017)

Expanding Stereochemical and Skeletal Diversity Using Petasis Reactions and 1,3-Dipolar Cycloadditions
por: Muncipinto, Giovanni, et al.
Publicado: (2010)

Synthesis and Stereochemical Assignment of (+)-Chamuvarinin
por: Florence, Gordon J., et al.
Publicado: (2010)

Stereochemical studies on pheromonal communications
por: MORI, Kenji
Publicado: (2014)

Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity
por: van der Vorm, Stefan, et al.
Publicado: (2018)

Doxorubicin and Aclarubicin: Shuffling Anthracycline Glycans for Improved Anticancer Agents
por: Wander, Dennis P. A., et al.
Publicado: (2020)

Stereochemical investigations on the biosynthesis of achiral (Z)-γ-bisabolene in Cryptosporangium arvum
por: Rinkel, Jan, et al.
Publicado: (2019)

Likelihood of atom–atom contacts in crystal structures of halogenated organic compounds
por: Jelsch, Christian, et al.
Publicado: (2015)

Synthesis and Oxidative Transformations of New Chiral Pinane-Type γ-Ketothiols: Stereochemical Features of Reactions
por: Lezina, Olga M., et al.
Publicado: (2021)

Total Synthesis and Stereochemical Assignment of (±)-Sorbiterrin A
por: Qi, Chao, et al.
Publicado: (2014)

Mimetics of ADP-Ribosylated Histidine through Copper(I)-Catalyzed Click Chemistry
por: Minnee, Hugo, et al.
Publicado: (2022)

Total Synthesis and Structural Studies of Zwitterionic Bacteroides fragilis Polysaccharide A1 Fragments
por: Wang, Zhen, et al.
Publicado: (2023)

Some Observations in the Use of Halogen Substituted Derivatives of Quinoline in Dermatological Practice
por: Chakravorty, A. N., et al.
Publicado: (1951)

Stereospecific suppression of active site mutants by methylphosphonate substituted substrates reveals the stereochemical course of site-specific DNA recombination
por: Rowley, Paul A., et al.
Publicado: (2015)

Quantification of Stereochemical Communication in Metal–Organic Assemblies
por: Castilla, Ana M., et al.
Publicado: (2016)

Cannot write session to /tmp/vufind_sessions/sess_g7654o7ujstu8hel4dbbh8hdui