Cargando…

Fluorine‐Induced Pseudo‐Anomeric Effects in Methoxycyclohexanes through Electrostatic 1,3‐Diaxial Interactions

We report counter‐intuitive axial preferences in non‐stereochemically biased, selectively fluorinated methoxycyclohexanes. These pseudo‐anomeric effects are apparent when electronegative CF(2) groups are placed at the C‐2, C‐4 and C‐6 positions of the cyclohexane ring to render the C‐3/5 axial hydro...

Descripción completa

Detalles Bibliográficos
Autores principales:	Piscelli, Bruno A., Sanders, William, Yu, Cihang, Al Maharik, Nawaf, Lebl, Thomas, Cormanich, Rodrigo A., O'Hagan, David
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	John Wiley and Sons Inc. 2020
Materias:	Communications
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7540582/ https://www.ncbi.nlm.nih.gov/pubmed/32588927 http://dx.doi.org/10.1002/chem.202003058

Ejemplares similares

Fluorine-containing substituents: metabolism of the α,α-difluoroethyl thioether motif
por: Rodil, Andrea, et al.
Publicado: (2019)

Fluorinated cyclohexanes: Synthesis of amine building blocks of the all-cis 2,3,5,6-tetrafluorocyclohexylamine motif
por: Bykova, Tetiana, et al.
Publicado: (2017)

Synthesis of organic liquid crystals containing selectively fluorinated cyclopropanes
por: Fang, Zeguo, et al.
Publicado: (2020)

Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs
por: Clark, Joshua L., et al.
Publicado: (2021)

Rhodium-catalyzed enantioselective and diastereodivergent access to diaxially chiral heterocycles
por: Wang, Yishou, et al.
Publicado: (2023)

Organo-fluorine chemistry II
por: O'Hagan, David
Publicado: (2010)

Organo-fluorine chemistry III
por: O'Hagan, David
Publicado: (2013)

Organo-fluorine chemistry V
por: O’Hagan, David
Publicado: (2021)

Themed series in organo-fluorine chemistry
por: O'Hagan, David
Publicado: (2008)

Aryl (β,β′,β″-Trifluoro)-tert-butyl: A Candidate Motif for the Discovery of Bioactives
por: Dobson, Luca S., et al.
Publicado: (2023)

Anomeric effect
por: Szarek, Walter A, et al.
Publicado: (1979)

Fluorinated Carbohydrates as Lectin Ligands: (19)F-Based Direct STD Monitoring for Detection of Anomeric Selectivity
por: Ribeiro, João P., et al.
Publicado: (2015)

Cyclohexyl Ketone Inhibitors of Pin1 Dock in a Trans-Diaxial Cyclohexane Conformation
por: Xu, Guoyan G., et al.
Publicado: (2012)

Janus Face All‐cis 1,2,4,5‐tetrakis(trifluoromethyl)‐ and All‐cis 1,2,3,4,5,6‐hexakis(trifluoromethyl)‐ Cyclohexanes
por: Yu, Cihang, et al.
Publicado: (2020)

Conformational signature of Ishikawa´s reagent using NMR information from diastereotopic fluorines
por: Andrade, Laize A F, et al.
Publicado: (2019)

The anomeric effect and associated stereoelectronic effects
por: Thatcher, Gregory R J
Publicado: (1993)

Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles
por: Launay, Guillaume G, et al.
Publicado: (2010)

New Polyporphyrin Arrays with Controlled Fluorescence Obtained by Diaxial Sn(IV)-Porphyrin Phenolates Chelation with Cu(2+) Cation
por: Mamardashvili, Galina M., et al.
Publicado: (2021)

Anomeric modification of carbohydrates using the Mitsunobu reaction
por: Hain, Julia, et al.
Publicado: (2018)

Selective anomeric acetylation of unprotected sugars in water
por: Lim, David, et al.
Publicado: (2017)

Mycothiol synthesis by an anomerization reaction through endocyclic cleavage
por: Manabe, Shino, et al.
Publicado: (2016)

Membrane property and biofunction of phospholiposome incorporated with anomeric galactolipids
por: Liu, Danyang, et al.
Publicado: (2016)

Anomeric Selectivity of Trehalose Transferase with Rare l-Sugars
por: Mestrom, Luuk, et al.
Publicado: (2020)

Is the Fluorine in Molecules Dispersive? Is Molecular Electrostatic Potential a Valid Property to Explore Fluorine-Centered Non-Covalent Interactions?
por: Varadwaj, Arpita, et al.
Publicado: (2019)

Anomericity of T-2 Toxin-glucoside: Masked Mycotoxin in Cereal Crops
por: McCormick, Susan P., et al.
Publicado: (2014)

Anomeric O-Functionalization of Carbohydrates for Chemical Conjugation to Vaccine Constructs
por: Park, Simon S., et al.
Publicado: (2018)

Stereoselective oxidative glycosylation of anomeric nucleophiles with alcohols and carboxylic acids
por: Yang, Tianyi, et al.
Publicado: (2018)

Selective Prebiotic Synthesis of α‐Threofuranosyl Cytidine by Photochemical Anomerization
por: Colville, Ben W. F., et al.
Publicado: (2021)

Fingerprinting, Antimicrobial, Antioxidant, Anticancer, Cyclooxygenase and Metabolic Enzymes Inhibitory Characteristic Evaluations of Stachys viticina Boiss. Essential Oil
por: Jaradat, Nidal, et al.
Publicado: (2019)

Phytochemical Profile, Antimicrobial, Cytotoxic, and Antioxidant Activities of Fresh and Air-Dried Satureja nabateorum Essential Oils
por: Al-Maharik, Nawaf, et al.
Publicado: (2021)

Enthalpies of Combustion and Formation of Severely Crowded Methyl-Substituted 1,3-dioxanes. The Magnitudes of 2,4- and 4,6-diaxial Me,Me-Interactions and the Chair–2,5-twist Energy Difference
por: Pihlaja, Kalevi, et al.
Publicado: (2020)

Molecular Recognition of Fluorine Impacts Substrate Selectivity in the Fluoroacetyl-CoA Thioesterase FlK
por: Weeks, Amy M., et al.
Publicado: (2014)

Selectively fluorinated cyclohexane building blocks: Derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane
por: Ayoup, Mohammed Salah, et al.
Publicado: (2015)

Selectively Fluorinated Citronellol Analogues Support a Hydrogen Bonding Donor Interaction with the Human OR1A1 Olfactory Receptor
por: He, Mengfan, et al.
Publicado: (2022)

The preferred conformation of erythro- and threo-1,2-difluorocyclododecanes
por: Wang, Yi, et al.
Publicado: (2012)

In vivo detection and replication studies of α-anomeric lesions of 2′-deoxyribonucleosides
por: Amato, Nicholas J., et al.
Publicado: (2015)

Recent Synthetic Approaches Toward Non-anomeric Spiroketals in Natural Products
por: Favre, Sylvain, et al.
Publicado: (2008)

The Impact of Leaving Group Anomericity on the Structure of Glycosyl Cations of Protected Galactosides
por: Greis, Kim, et al.
Publicado: (2020)

Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams
por: Więcław, Michał Mateusz, et al.
Publicado: (2021)

Skeletal Editing—Nitrogen Deletion of Secondary Amines by Anomeric Amide Reagents
por: Zippel, Christoph, et al.
Publicado: (2021)

Cannot write session to /tmp/vufind_sessions/sess_53dg29gbu1mjf6ngf1vit22bqm