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View article: Recent advances in the construction of quaternary pseudoanomeric centers in <i>gem-C</i>,<i>C</i>-glycosides: from zaragozic acids to remdesivir
Recent advances in the construction of quaternary pseudoanomeric centers in <i>gem-C</i>,<i>C</i>-glycosides: from zaragozic acids to remdesivir Open
This review outlines recent advances in synthesizing gem-C , C -glycosides ( i.e. , glycomimetics with quaternary pseudo-anomeric centers), emphasizing innovative approaches like C–H activation and HAT methods.
View article: Gold(I)-Catalyzed Reactions of <i>exo</i>-Glycals with Propargyl Esters toward C-1 Alkenyl Spirocyclopropyl Carbohydrates
Gold(I)-Catalyzed Reactions of <i>exo</i>-Glycals with Propargyl Esters toward C-1 Alkenyl Spirocyclopropyl Carbohydrates Open
An atom-economic and diazo-free strategy for the construction of novel pseudo anomeric C-1 alkenyl spirocyclopropyl sugars is described. Leveraging the 1,2-migration pathway of propargyl esters under gold(I) catalysis, easily available exo…
View article: Deconstructing Best‐in‐Class Neoglycoclusters as a Tool for Dissecting Key Multivalent Processes in Glycosidase Inhibition
Deconstructing Best‐in‐Class Neoglycoclusters as a Tool for Dissecting Key Multivalent Processes in Glycosidase Inhibition Open
Multivalency represents an appealing option to modulate selectivity in enzyme inhibition and transform moderate glycosidase inhibitors into highly potent ones. The rational design of multivalent inhibitors is however challenging because gl…
View article: Expanding the scope of the successive ring expansion strategy for macrocycle and medium-sized ring synthesis: unreactive and reactive lactams
Expanding the scope of the successive ring expansion strategy for macrocycle and medium-sized ring synthesis: unreactive and reactive lactams Open
New Successive Ring Expansion (SuRE) protocols are described for use on unreactive lactams, as well as iminosugar derived lactams.
View article: Diastereoselective access to <i>C</i>,<i>C</i>-glycosyl amino acids <i>via</i> iron-catalyzed, auxiliary-enabled MHAT coupling
Diastereoselective access to <i>C</i>,<i>C</i>-glycosyl amino acids <i>via</i> iron-catalyzed, auxiliary-enabled MHAT coupling Open
Novel C , C -glycosyl amino acids were accessed by means of an iron-catalyzed hydrogen atom transfer sequence. Crucially, two-fold diastereocontrol could be achieved in the ‘matched’ coupling of exo - d -glycals with an enantiopure dehydro…
View article: Towards a General Access to 1‐Azaspirocyclic Systems via Photoinduced, Reductive Decarboxylative Radical Cyclizations
Towards a General Access to 1‐Azaspirocyclic Systems via Photoinduced, Reductive Decarboxylative Radical Cyclizations Open
A convenient and versatile approach to important 1‐azaspirocyclic systems relevant to medicinal chemistry and natural products is reported herein. The main strategy relies on a reductive decarboxylative cyclization of redox‐active esters w…
View article: Dissecting Key Multivalent Processes in Glycosidase Inhibition: Insights from Thermodynamic Modelling and Atomistic Simulations
Dissecting Key Multivalent Processes in Glycosidase Inhibition: Insights from Thermodynamic Modelling and Atomistic Simulations Open
Multivalency represents a powerful approach to increase the inhibition potency of moderate glycosidase inhibitors. Regarding the key role of catalytic glycoside hydrolysis in biology, understanding the molecular mechanisms and origin of th…
View article: Recent Applications of Hexamethyldisilathiane (TMS2S) in Organic Synthesis
Recent Applications of Hexamethyldisilathiane (TMS2S) in Organic Synthesis Open
View article: Bambus[4,6]urils as Dual Scaffolds for Multivalent Iminosugar Presentation and Ion Transport: Access to Unprecedented Glycosidase-Directed Anion Caging Agents
Bambus[4,6]urils as Dual Scaffolds for Multivalent Iminosugar Presentation and Ion Transport: Access to Unprecedented Glycosidase-Directed Anion Caging Agents Open
Bambusurils, BU[4] and BU[6], were used for the first time as multivalent scaffolds to link glycosidases inhibitors derived from 1-deoxynojirimycin (DNJ). Two linear DNJ ligands having six or nine carbon alkyl azido linkers or a trivalent …
View article: Hybrid Multivalent Jack Bean α-Mannosidase Inhibitors: The First Example of Gold Nanoparticles Decorated with Deoxynojirimycin Inhitopes
Hybrid Multivalent Jack Bean α-Mannosidase Inhibitors: The First Example of Gold Nanoparticles Decorated with Deoxynojirimycin Inhitopes Open
Among carbohydrate-processing enzymes, Jack bean α-mannosidase (JBα-man) is the glycosidase with the best responsiveness to the multivalent presentation of iminosugar inhitopes. We report, in this work, the preparation of water dispersible…
View article: Synthesis and Glycosidase Inhibition Properties of Calix[8]arene-Based Iminosugar Click Clusters
Synthesis and Glycosidase Inhibition Properties of Calix[8]arene-Based Iminosugar Click Clusters Open
A set of 6- to 24-valent clusters was constructed with terminal deoxynojirimycin (DNJ) inhibitory heads through C6 or C9 linkers by way of Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions between mono- or trivalent azido-armed …
View article: Stereoselective Synthesis of <i>C</i>,<i>C</i>-Glycosides from <i>exo</i>-Glycals Enabled by Iron-Mediated Hydrogen Atom Transfer
Stereoselective Synthesis of <i>C</i>,<i>C</i>-Glycosides from <i>exo</i>-Glycals Enabled by Iron-Mediated Hydrogen Atom Transfer Open
We describe herein a convenient strategy for the construction of C,C-glycoside building blocks via the intermediacy of tertiary pseudoanomeric radicals. Application of an iron-mediated hydrogen atom transfer/Michael-Giese coupling enables …
View article: Conformationally constrained fused bicyclic iminosugars: synthetic challenges and opportunities
Conformationally constrained fused bicyclic iminosugars: synthetic challenges and opportunities Open
This review presents an overview of the synthetic approaches developed towards the preparation of fused bicyclic iminosugars containing a three or four-membered ring, as well as their biological activity whenever such data are available.Ch…
View article: Selective Targeting of the Interconversion between Glucosylceramide and Ceramide by Scaffold Tailoring of Iminosugar Inhibitors
Selective Targeting of the Interconversion between Glucosylceramide and Ceramide by Scaffold Tailoring of Iminosugar Inhibitors Open
A series of simple C-alkyl pyrrolidines already known as cytotoxic inhibitors of ceramide glucosylation in melanoma cells can be converted into their corresponding 6-membered analogues by means of a simple ring expansion. This study illust…
View article: Glycomimetics: Design, Synthesis, and Therapeutic Applications
Glycomimetics: Design, Synthesis, and Therapeutic Applications Open
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View article: Structural Basis of Outstanding Multivalent Effects in Jack Bean α‐Mannosidase Inhibition
Structural Basis of Outstanding Multivalent Effects in Jack Bean α‐Mannosidase Inhibition Open
Multivalent design of glycosidase inhibitors is a promising strategy for the treatment of diseases involving enzymatic hydrolysis of glycosidic bonds in carbohydrates. An essential prerequisite for successful applications is the atomic‐lev…
View article: One-Pot, Highly Stereoselective Synthesis of Dithioacetal-α,α-Diglycosides
One-Pot, Highly Stereoselective Synthesis of Dithioacetal-α,α-Diglycosides Open
A one-step access to dithioacetal-α,α-diglycosides is reported. The synthetic strategy is based on the thioacetalization of aldehydes or ketones via highly stereoselective ring-opening of 1,6 anhydrosugars with bis(trimethylsilyl)sulfide.
View article: CCDC 1832560: Experimental Crystal Structure Determination
CCDC 1832560: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Correction: Stereodivergent synthesis of right- and left-handed iminoxylitol heterodimers and monomers. Study of their impact on β-glucocerebrosidase activity
Correction: Stereodivergent synthesis of right- and left-handed iminoxylitol heterodimers and monomers. Study of their impact on β-glucocerebrosidase activity Open
Correction for ‘Stereodivergent synthesis of right- and left-handed iminoxylitol heterodimers and monomers. Study of their impact on β-glucocerebrosidase activity’ by Fabien Stauffert et al., Org. Biomol. Chem., 2017, 15, 3681–3705.
View article: Pushing the limits of catalytic C–H amination in polyoxygenated cyclobutanes
Pushing the limits of catalytic C–H amination in polyoxygenated cyclobutanes Open
The limits of catalytic C–H amination were explored in polyoxygenated cyclobutanes to access original spiranic iminosugars of biological interest.
View article: Understanding multivalent effects in glycosidase inhibition using C-glycoside click clusters as molecular probes
Understanding multivalent effects in glycosidase inhibition using C-glycoside click clusters as molecular probes Open
Multivalent C-glycosides based on C60 or β-cyclodextrin cores were designed to probe the influence of inhitopes in glycosidase binding events.
View article: Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores
Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores Open
The synthesis and photophysical properties of the first examples of iminosugar clusters based on a BODIPY or a pyrene core are reported. The tri- and tetravalent systems designed as molecular probes and synthesized by way of Cu(I)-catalyse…