Journal ArticleDOI
Recent Advances in the Chemical Synthesis of C-Glycosides
TLDR
Mechanistically, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes, which are discussed as subcategories under each type of sugar precursor.Abstract:
Advances in the chemical synthesis of C-pyranosides/furanosides are summarized, covering the literature from 2000 to 2016. The majority of the methods take advantage of the construction of the glycosidic C—C bond. These C-glycosylation methods are categorized herein in terms of the glycosyl donor precursors, which are commonly used in O-glycoside synthesis and are easily accessible to nonspecialists. They include glycosyl halides, glycals, sugar acetates, sugar lactols, sugar lactones, 1,2-anhydro sugars, thioglycosides/sulfoxides/sulfones, selenoglycosides/telluroglycosides, methyl glycosides, and glycosyl imidates/phosphates. Mechanistically, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes, which are discussed as subcategories under each type of sugar precursor. Moreover, intramolecular rearrangements, such as the Claisen rearrangement, Ramberg–Backlund rearrangement, and 1,2-Wittig rearrangement, which usuall...read more
Citations
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Recent advances of 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) in photocatalytic transformations.
TL;DR: In this review, the recent advances of the application of 4CzIPN as a photoredox catalyst in the past three years (2016-2018) for various organic reactions are summarized.
Journal ArticleDOI
Methods for 2-Deoxyglycoside Synthesis.
Clay S. Bennett,M. Carmen Galan +1 more
TL;DR: This Review covers classical approaches to deoxyglycoside synthesis, as well as more recently developed chemistry that aims to control the selectivity of the reaction through rational design of the promoter.
Journal ArticleDOI
Cross-Electrophile Couplings of Activated and Sterically Hindered Halides and Alcohol Derivatives.
TL;DR: This Account summarizes synthetic methods that allow formation of valuable C-C bonds using challenging electrophiles but also provides insight into the relationship between the structure and reactivity of the substrates and catalysts, as well as the effects of additives.
Journal ArticleDOI
Synthesis of Reversed C‐Acyl Glycosides through Ni/Photoredox Dual Catalysis
TL;DR: A practical, scalable, and versatile route for the synthesis of non-anomeric and unexploited C-acyl glycosides through a Ni/photoredox dual catalytic system, utilizing an organic photocatalyst.
Journal ArticleDOI
Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis.
TL;DR: This Review is a comprehensive overview of reactions catalyzed by nickel and an added bidentate phosphine, focusing on the steps transforming the combination of precatalyst and ligand into an active catalyst and the potential effects of this transformation on nickel catalysis.
References
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Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp3-carbons with aryl halides
Zhiwei Zuo,Derek T. Ahneman,Lingling Chu,Jack A. Terrett,Abigail G. Doyle,David W. C. MacMillan +5 more
TL;DR: In this article, the synergistic combination of photoredox catalysis and nickel catalysis was used to achieve a direct decarboxylative sp(3)-sp(2) cross-coupling of amino acids with aryl halides.
Journal ArticleDOI
New principles for glycoside-bond formation.
Xiangming Zhu,Richard R. Schmidt +1 more
TL;DR: New principles for the formation of glycoside bonds are discussed and developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.
Journal ArticleDOI
SGLT2 inhibition — a novel strategy for diabetes treatment
Edward C Chao,Robert R. Henry +1 more
TL;DR: The role of SGLT2 in glucose homeostasis and the evidence available so far on the therapeutic potential of blocking these transporters in the treatment of diabetes are discussed.
Journal ArticleDOI
Discovery of Dapagliflozin: A Potent, Selective Renal Sodium-Dependent Glucose Cotransporter 2 (SGLT2) Inhibitor for the Treatment of Type 2 Diabetes
Wei Meng,Bruce A. Ellsworth,Alexandra A. Nirschl,P.J. McCann,Manorama Patel,Ravindar N. Girotra,Gang Wu,Philip M. Sher,Eamonn P. Morrison,Scott A. Biller,Robert Zahler,Prashant P. Deshpande,Annie Pullockaran,Deborah Hagan,Nathan Morgan,Joseph R. Taylor,Mary T. Obermeier,William G. Humphreys,Ashish Khanna,Lorell Discenza,James G. Robertson,Aiying Wang,Songping Han,John R. Wetterau,Evan B. Janovitz,Oliver P. Flint,Jean M. Whaley,William N. Washburn +27 more
TL;DR: The C-aryl glucoside 6 (dapagliflozin) was identified as a potent and selective hSGLT2 inhibitor which reduced blood glucose levels in a dose-dependent manner by as much as 55% in hyperglycemic streptozotocin (STZ) rats.