title: Automatized Assessment of Protective Group Reactivity: A Step Toward Big Reaction Data Analysis.
abstract: We report a new method to assess protective groups (PGs) reactivity as a function of reaction conditions (catalyst, solvent) using raw reaction data. It is based on an intuitive similarity principle for chemical reactions: similar reactions proceed under similar conditions. Technically, reaction similarity can be assessed using the Condensed Graph of Reaction (CGR) approach representing an ensemble of reactants and products as a single molecular graph, i.e., as a pseudomolecule for which molecular descriptors or fingerprints can be calculated. CGR-based in-house tools were used to process data for 142,111 catalytic hydrogenation reactions extracted from the Reaxys database. Our results reveal some contradictions with famous Greene's Reactivity Charts based on manual expert analysis. Models developed in this study show high accuracy (ca. 90%) for predicting optimal experimental conditions of protective group deprotection.
authors: Laboratory of Chemoinformatics and Molecular Modeling, Department of Organic Chemistry, A.M. Butlerov Institute of Chemistry, Kazan Federal University , Kremlyovskaya Str. 18, Kazan, Russia , 420008.|Laboratory of Chemoinformatics, Faculty of Chemistry, University of Strasbourg , rue Blaise Pascal 1, Strasbourg, France , 67000.
authors: Arkadii I
authors: AI
authors: Lin
authors: Laboratory of Chemoinformatics and Molecular Modeling, Department of Organic Chemistry, A.M. Butlerov Institute of Chemistry, Kazan Federal University , Kremlyovskaya Str. 18, Kazan, Russia , 420008.
authors: Timur I
authors: TI
authors: Madzhidov
authors: Laboratory of Chemoinformatics, Faculty of Chemistry, University of Strasbourg , rue Blaise Pascal 1, Strasbourg, France , 67000.
authors: Olga
authors: O
authors: Klimchuk
authors: Laboratory of Chemoinformatics and Molecular Modeling, Department of Organic Chemistry, A.M. Butlerov Institute of Chemistry, Kazan Federal University , Kremlyovskaya Str. 18, Kazan, Russia , 420008.
authors: Ramil I
authors: RI
authors: Nugmanov
authors: Laboratory of Chemoinformatics and Molecular Modeling, Department of Organic Chemistry, A.M. Butlerov Institute of Chemistry, Kazan Federal University , Kremlyovskaya Str. 18, Kazan, Russia , 420008.
authors: Igor S
authors: IS
authors: Antipin
authors: Laboratory of Chemoinformatics and Molecular Modeling, Department of Organic Chemistry, A.M. Butlerov Institute of Chemistry, Kazan Federal University , Kremlyovskaya Str. 18, Kazan, Russia , 420008.|Laboratory of Chemoinformatics, Faculty of Chemistry, University of Strasbourg , rue Blaise Pascal 1, Strasbourg, France , 67000.
authors: Alexandre
authors: A
authors: Varnek
mesh_terms: D001331:Automation; D002384:Catalysis; D016208:Databases, Factual; D006878:Hydroxides / Q000737:chemistry; D048088:Informatics / Q000379:methods*; D008956:Models, Chemical; D010636:Phenols / Q000737:chemistry; D012997:Solvents / Q000737:chemistry
chemical_list: D006878:Hydroxides; D010636:Phenols; D012997:Solvents; C031356:hydroxide ion