A range of unprocessed, reducing sugar substrates (mono‐, di‐ and trisaccharides) is shown to enter a straightforward 4‐step synthetic route to water‐soluble, uncharged BODIPY derivatives with unimpaired chiral integrity and high fluorescence efficiency. A wide compatibility to several postfunctionalizations is demonstrated suggesting an universal utility of the multifunctional glycoconjugate, which we call GlycoBODIPY. Knoevenagel condensations are able to promote a red‐shift, furnishing strongly fluorescent red and far‐red glycoconjugates of high hydrophilicity. The synthetic outcome was studied by X‐ray crystallography and by comprehensive photophysical investigations in several solvent systems. Furthermore, cell experiments underline an efficient cell uptake and demonstrate differential cell targeting as a function of the integrated chiral information.
Messaoudi
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GlycoBODIPYs: Sugars Serving as Natural Stock for Water‐soluble Fluorescent Probes of Complex Chiral Morphology
[ASAP] Diastereoselective Pd-Catalyzed Anomeric C(sp3)–H Activation: Synthesis of α-(Hetero)aryl C-Glycosides
C(sp3)−C(sp3) Cross‐Coupling of Alkyl Bromides and Ethers Mediated by Metal and Visible Light Photoredox Catalysis
Abstract
We report a C(sp 3)−C(sp 3) cross‐coupling of alkyl bromides and alkyl chlorides with ethers by dual photoredox‐nickel catalysis. The catalytic system comprises of the organic photocatalyst 1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6‐dicyanobenzene (4‐CzIPN) and bench stable nickel (II) acetylacetonate in the presence of visible‐light, providing the coupling products in up to 92% yield. Preliminary mechanistic studies suggest two catalytic cycles, as well as the photogeneration of bromine or chlorine radicals from halide atoms that are present in the structures of the coupling partners. The halide radical mediates the hydrogen atom transfer event, avoiding the need of an additional HAT catalyst.
[ASAP] Genetically Encoding Fluorosulfate-l-tyrosine To React with Lysine, Histidine, and Tyrosine via SuFEx in Proteins in Vivo
Direct Catalytic Alcoholysis of Unactivated 8-Aminoquinoline Amides
Glycan-based diagnostic devices: current progress, challenges and perspectives
DOI: 10.1039/C5CC06876B, Feature Article
The development of glycan-based diagnostic devices is illustrated with recent examples from both carbohydrate recognition and device design aspects.
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An improved method for the large scale preparation of α,α′-trehalose-6-phosphate
Source:Tetrahedron Letters, Volume 56, Issue 23
Author(s): Chunliang Liu , Patrick S. Mariano
An improved method was developed for the efficient, large-scale synthesis of α,α′-trehalose-6-phosphate starting with α,α′-trehalose. In the sequence, octa-trimethylsilylation of α,α′-trehalose is followed by selective removal of the 6-O-trimethylsilyl protecting group. Reaction of the mono-alcohol with (PhO)2POCl is then followed by simultaneous hydrogenolysis and per-desilylation to generate α,α′-trehalose-6-phosphate, free of contamination by inorganic phosphate.
Graphical abstract
Highly Electron-Rich Pincer-Type Iron Complexes Bearing Innocent Bis(metallylene)pyridine Ligands: Syntheses, Structures, and Catalytic Activity
Primary Amines by Transfer Hydrogenative Reductive Amination of Ketones by Using Cyclometalated IrIII Catalysts
Abstract
Cyclometalated iridium complexes are found to be versatile catalysts for the direct reductive amination (DRA) of carbonyls to give primary amines under transfer-hydrogenation conditions with ammonium formate as both the nitrogen and hydrogen source. These complexes are easy to synthesise and their ligands can be easily tuned. The activity and chemoselectivity of the catalyst towards primary amines is excellent, with a substrate to catalyst ratio (S/C) of 1000 being feasible. Both aromatic and aliphatic primary amines were obtained in high yields. Moreover, a first example of homogeneously catalysed transfer-hydrogenative DRA has been realised for β-keto ethers, leading to the corresponding β-amino ethers. In addition, non-natural α-amino acids could also be obtained in excellent yields with this method.
Reduce the work! A broad range of ketones have been successfully aminated to afford primary amines under transfer-hydrogenation conditions by using ammonium formate as the amine source and 0.1 mol % of a cyclometalated IrIII catalyst (see scheme).
Copper-Catalyzed Domino Cycloaddition/CN Coupling/Cyclization/(CH Arylation): An Efficient Three-Component Synthesis of Nitrogen Polyheterocycles
A cat of all trades: A single copper catalyst promoted up to three reaction steps with separate catalytic cycles in a domino sequence (azide–alkyne cycloaddition/Goldberg amidation/Camps cyclization/(C![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
H arylation)) for the rapid construction of complex heterocycles from three simple components under mild conditions (see scheme). Facile cleavage of the triazole ring enables further elaboration of the condensation products.