Fluorine-Directed Glycosylation Enables the Stereocontrolled Synthesis of Selective SGLT2 Inhibitors for Type II Diabetes.

No abstract is available for this paper.

• Publication year

  2018

• Venue

  Chemistry

• Publication date

  2018-02-26

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/chem.201705373PMID 29211300
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• The Fluorine Gauche Effect: A Brief History

  2017cited by this paper
• Renal, metabolic and cardiovascular considerations of SGLT2 inhibition

  2017cited by this paper
• Catalytic, Vicinal Difluorination of Olefins: Creating a Hybrid, Chiral Bioisostere of the Trifluoromethyl and Ethyl Groups

  2016cited by this paper
• Total Synthesis of the Proposed Structure of Ardimerin, and Proposal for its Structural Revision

  2016cited by this paper
• Total Synthesis of (+)-Vicenin-2.

  2016cited by this paper
• Fluorine-directed 1,2-trans glycosylation of rare sugars.

  2016cited by this paper
• Recent Developments of C-Aryl Glucoside SGLT2 Inhibitors.

  2016cited by this paper
• Applications of Fluorine in Medicinal Chemistry.

  2015cited by this paper
• Delineating the physical organic profile of the 6-fluoro glycosyl donor

  2015cited by this paper
• Comparative Analysis of Fluorine-Directed Glycosylation Selectivity: Interrogating C2 [OH F] Substitution in d-­Glucose and d-Galactose

  2015cited by this paper
• Exploration of fluorine chemistry at the multidisciplinary interface of chemistry and biology.

  2013cited by this paper
• SGLT2 inhibitors enter crowded diabetes space

  2013cited by this paper
• Fluorine-directed β-galactosylation: chemical glycosylation development by molecular editing.

  2012cited by this paper
• SGLT2 inhibitors race to enter type-2 diabetes market

  2012cited by this paper
• Konformative Fluoreffekte in der Organokatalyse: eine neuartige Strategie zum molekularen Design

  2011cited by this paper
• Fluorine conformational effects in organocatalysis: an emerging strategy for molecular design.

  2011cited by this paper
• Development and potential role of type-2 sodium-glucose transporter inhibitors for management of type 2 diabetes

  2011cited by this paper
• Glucose transport by human renal Na+/D-glucose cotransporters SGLT1 and SGLT2.

  2011cited by this paper
• C-Aryl glycoside inhibitors of SGLT2: Exploration of sugar modifications including C-5 spirocyclization.

  2010cited by this paper
• Fluorine-directed glycosylation.

  2010cited by this paper
• The C–F bond as a conformational tool in organic and biological chemistry

  2010cited by this paper
• Synthesis and SAR of Benzisothiazole- and Indolizine-β-d-glucopyranoside Inhibitors of SGLT2.

  2010cited by this paper
• Fluorine in health care: Organofluorine containing blockbuster drugs

  2010cited by this paper
• From victim to ally: the kidney as an emerging target for the treatment of diabetes mellitus

  2009cited by this paper
• From victim to ally: the kidney as an emerging target for the treatment of diabetes mellitus.

  2009cited by this paper
• Evolution of sodium glucose co-transporter 2 inhibitors as anti-diabetic agents

  2009cited by this paper
• Development of the renal glucose reabsorption inhibitors: a new mechanism for the pharmacotherapy of diabetes mellitus type 2.

  2009cited by this paper
• Discovery of dapagliflozin: a potent, selective renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.

  2008cited by this paper
• Understanding organofluorine chemistry. An introduction to the C-F bond.

  2008cited by this paper
• Remogliflozin Etabonate, in a Novel Category of Selective Low-Affinity Sodium Glucose Cotransporter (SGLT2) Inhibitors, Exhibits Antidiabetic Efficacy in Rodent Models

  2008cited by this paper
• Fluorine in medicinal chemistry.

  2008cited by this paper
• The role of fluorine in medicinal chemistry

  2007cited by this paper
• Fluorine in Pharmaceuticals: Looking Beyond Intuition

  2007cited by this paper
• Diabetes update.

  2006cited by this paper
• Type 2 diabetes market

  2005cited by this paper
• A missense mutation in the Na(+)/glucose cotransporter gene SGLT1 in a patient with congenital glucose-galactose malabsorption: normal trafficking but inactivation of the mutant protein.

  2001cited by this paper
• The human kidney low affinity Na+/glucose cotransporter SGLT2. Delineation of the major renal reabsorptive mechanism for D-glucose.

  1994cited by this paper
• Inactivation of a beta-glucosidase through the accumulation of a stable 2-deoxy-2-fluoro-alpha-D-glucopyranosyl-enzyme intermediate: a detailed investigation.

  1992cited by this paper
• Glucose/galactose malabsorption caused by a defect in the Na+/glucose cotransporter

  1991cited by this paper
• Theoretical evidence in support of the Anh–Eisenstein electronic model in controlling π-facial stereoselectivity in nucleophilic additions to carbonyl compounds

  1990cited by this paper
• The synthesis and hydrolysis of a series of deoxyfluoro-d-glucopyranosyl phosphates

  1986cited by this paper

• A novel gentiopicroside derivative clears phosphorylation tau to improve memory of AD mice by targeting AMPK and increase of gut neuroprotective metabolites.

  2026cites this paper
• Medicinal chemistry advances of SGLT inhibitors: SAR, structural innovation, and mechanistic insights.

  2026cites this paper
• Expeditious Synthesis of 2-Deoxy-2-perfluoroalkyl Glycosides.

  2026cites this paper
• Stereoselective Assembly of 2-Deoxy-2-fluoroglycosides Enabled by Pyridinium Catalysis.

  2026cites this paper
• Origami with small molecules: exploiting the C–F bond as a conformational tool

  2025cites this paper
• AuCl3-tBuCN Catalysis in 1,2-trans 2-Deoxy-2-fluoro Glycosidic Bond Formation.

  2025cites this paper
• A Novel Gastrodin Derivative with Neuroprotection Promotes NGF-Mimic Activity by Targeting INSR and ACTN4 to Activate PI3K/Akt Signaling Pathway in PC12 Cells

  2025cites this paper
• Accumulation, Characterization and Reactivity of Chiral Ammonium-Carboxonium Dications in Superacid.

  2024cites this paper
• Silver-Catalyzed Coupling of Unreactive Carboxylates: Synthesis of α-Fluorinated O-Aryl Esters.

  2024cites this paper
• Expanding the Scope of C-Glycoside Synthesis from Unstable Organolithium Reagents Using Flow Microreactors.

  2024cites this paper
• Discovery of Orally Bioavailable FmlH Lectin Antagonists as Treatment for Urinary Tract Infections.

  2024cites this paper
• Stereoselective access to 2-deoxy-2-trifluoromethyl sugar mimetics by trifluoromethyl-directed 1,2-trans glycosylation

  2023cites this paper
• Drug Discovery Based on Fluorine-Containing Glycomimetics

  2023cites this paper
• Fluorinated carbohydrates for 18F-positron emission tomography (PET)

  2023cites this paper
• Fluoro-labelled sp2-iminoglycolipids with immunomodulatory properties.

  2023cites this paper
• Formal Glycosylation of Quinones with exo-Glycals Enabled by Iron-Mediated Oxidative Radical-Polar Crossover.

  2022cites this paper
• Fluorine‐Directed Automated Mannoside Assembly

  2022cites this paper
• Stereospecific/stereoselective Nickel catalyzed reductive cross-coupling: An efficient tool for the synthesis of biological active targeted molecules

  2022cites this paper
• Highly regioselective and stereoselective synthesis of C-Aryl glycosides via nickel-catalyzed ortho-C-H glycosylation of 8-aminoquinoline benzamides.

  2021cites this paper
• Fluorinated Rings: Conformation and Application.

  2021cites this paper
• Diastereoselective Pd-Catalyzed Anomeric C(sp3)–H Activation: Synthesis of α-(Hetero)aryl C-Glycosides

  2021cites this paper
• Multisubstituted pyrazole synthesis via [3 + 2] cycloaddition/rearrangement/N H insertion cascade reaction of α-diazoesters and ynones

  2020cites this paper
• Syntheses of SGLT2 Inhibitors by Ni- and Pd-Catalyzed Fukuyama Coupling Reactions.

  2020cites this paper
• The role of fluorine in glycomimetic drug design.

  2020cites this paper
• Total Chemical Syntheses of the GM3 and F-GM3 Ganglioside Epitopes and Comparative Pre-Clinical Evaluation for Non-Invasive Imaging of Oligodendrocyte Differentiation.

  2020cites this paper
• Nickel-catalyzed reductive coupling of glucosyl halides with aryl/vinyl halides enabling β-selective preparation of C-aryl/vinyl glucosides

  2019cites this paper
• Structural and Computational Analysis of 2-Halogeno-Glycosyl Cations in Superacid: An extansive Platform.

  2019cites this paper
• In the Search of Glycoside-Based Molecules as Antidiabetic Agents

  2019cites this paper
• Synthetic strategies for fluorination of carbohydrates.

  2019cites this paper
• Spiroketal Phthalane C-Glycosides: Synthesis of Papulacandins and SGLT2 Inhibitors

  2019cites this paper
• Stereospecific α-Sialylation by Site-Selective Fluorination.

  2019cites this paper
• Positive-unlabelled learning of glycosylation sites in the human proteome

  2019cites this paper
• Plateforme modulable pour le développement de glycolipides à potentiel immunoadjuvant

  2019cites this paper
• Bioisosteres of Carbohydrate Functional Groups in Glycomimetic Design

  2019cites this paper
• Structural and Computational Analysis of 2‐Halogeno‐Glycosyl Cations in the Presence of a Superacid: An Expansive Platform

  2019cites this paper
• Evidence of Phosphonium-Carbenium Dication Formation in a Superacid: Precursor to Fluorinated Phosphine Oxides.

  2018cites this paper
• Stereocontrolled Synthesis of 2‐Fluorinated C‐Glycosides

  2018cites this paper
• Reengineering Chemical Glycosylation: Direct, Metal-Free Anomeric O-Arylation of Unactivated Carbohydrates.

  2018cites this paper