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Carbohydrates Momciloˇ Miljkovic´ Carbohydrates Momciloˇ Miljkovic´ Carbohydrates Synthesis, Mechanisms, and Stereoelectronic Effects 123 Momciloˇ Miljkovic´ Department of Biochemistry & Molecular Biology Pennsylvania State University Milton S. Hershey Medical Center 500 University Drive Hershey PA 17033 H171 USA [email protected] ISBN 978-0-387-92264-5 e-ISBN 978-0-387-92265-2 DOI 10.1007/978-0-387-92265-2 Springer New York Dordrecht Heidelberg London Library of Congress Control Number: 2009933276 © Springer Science+Business Media, LLC 2010 All rights reserved. This work may not be translated or copied in whole or in part without the written permission of the publisher (Springer Science+Business Media, LLC, 233 Spring Street, New York, NY 10013, USA), except for brief excerpts in connection with reviews or scholarly analysis. Use in connection with any form of information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed is forbidden. The use in this publication of trade names, trademarks, service marks, and similar terms, even if they are not identified as such, is not to be taken as an expression of opinion as to whether or not they are subject to proprietary rights. Printed on acid-free paper Springer is part of Springer Science+Business Media (www.springer.com) Dedicated to the memory of Professors Milivoje S. Lozani´c and Djordje Stefanovi´c University of Belgrade, Serbia Foreword The development of organic chemistry over the last 40 years has been absolutely phenomenal, particularly the deepened understanding of chemical reactivity, molec- ular construction, and tools for analysis and purification. Without doubt, carbohy- drate chemistry has played a major role in this historic advance and in the future will have crucial ramifications in most areas of biomedical research into the functioning of Nature at the molecular level. This book covers all basic carbohydrate chemistry, including most important synthetic methods and reaction mechanisms and notably takes into account the prin- ciple of stereoelectronic effect which has played a key role in understanding the con- formation and chemical reactivity of this important class of natural product. Even nomenclature has been properly covered and it is fair to say that all the key refer- ences of carbohydrates have been cited. Such a book could only have been written by an expert who has spent his entire research career in this area. This book of Momciloˇ Miljkovic´ will be of interest not only to specialists in the field, but also to synthetic chemists in general. This book also contains most of the material needed for a graduate course in carbohydrate chemistry. Furthermore, it should be particularly valuable for investigators working in various aspects of bioorganic chemistry including the discovery of new medicines. Quebec, Canada Pierre Deslongchamps, FRS, FRSC vii Preface Carbohydrates are one of the three most important components of living cells (the other two being amino acids and lipids). In order to understand their biochemical behavior one must understand steric and electronic factors that control their reactiv- ity and chemistry. Two properties of carbohydrates that are most important for their chemical behavior are their shape (conformation) and stereoelectronic interactions that are unique and characteristic for each carbohydrate structure. So chapters on anomeric effect, a very important electronic effect first discov- ered in studies of carbohydrates and later found to be of general importance in many other organic molecules, glycosidic bond hydrolysis, isomerization of free carbohy- drates in aqueous solution, relative reactivity of hydroxyl groups in a carbohydrate molecule, nucleophilic displacement with or without change of the configuration at the reacting carbon atom, addition of nucleophiles to glycopyranosiduloses, etc., are all to a various extent related to stereoelectronic effects that exist in carbohydrate structures. Cyclic acetals and ketals and anhydrosugars are both very important intermedi- ates in synthetic carbohydrate chemistry, first being used for protection of hydroxyl groups that are not supposed to take part in further chemical transformation of the intermediate and second being used as synthetic intermediates in carbohydrate chemistry because they can serve as starting materials for the synthesis of many dif- ferent carbohydrate derivatives, for example, the amino sugars, the branched chain sugars, oligosaccharides. The amino sugars, being important components of many biomolecules such as glycosaminoglycans, heparin, chondroitin as well as many natural products, such as sugar-based antibiotics, macrolide antibiotics, are dis- cussed in a separate chapter. The last three chapters of the book deal with topics not usually found in car- bohydrate chemistry texts like this one, although according to the author’s opinion they are very important and they are unjustly neglected. These are carbohydrate- based antibiotics, synthesis of polychiral natural products from carbohydrates, and chemistry of higher-carbon carbohydrates. Much attention has been paid to the mechanisms of various carbohydrate reac- tions as well as to the role of stereoelectronic effects that they play in the reac- tivity of carbohydrates and the stereochemical outcome of various carbohydrate reactions. ix x Preface In the end, I wish to express my deep gratitude to Professor Pierre Des- longchamps for taking time to read the entire book and provide me with invaluable comments and critique. I would also like to thank my wife, Irina Miljkovic,´ for her patience and understanding throughout my scientific life. Contents 1 Introduction .............................. 1 Stereochemistry . ............................ 2 Representation of Monosaccharides .................. 2 Acyclic Form of Monosaccharides ................. 2 Cyclic Forms of Monosaccharides .................. 4 The Nomenclature of Carbohydrates .................. 9 TrivialNames............................ 9 StemandSystematicNames..................... 9 Conventions............................. 10 Choice of Parent Monosaccharides ................. 10 Choice Between Alternative Names for Substituted Derivatives . 11 Configurational Symbols and Prefixes . ............. 11 Ketoses................................ 13 Deoxy-monosaccharides ....................... 14 Amino-monosaccharides ....................... 15 O-Substitution ............................ 15 AcyclicForms............................ 17 Anomers and the Anomeric Configurational Symbols (“α”or“β”).............................. 18 Glycosides . ............................ 19 Glycosyl Radicals and Glycosylamines . ............. 20 Aldonic Acids ............................ 21 UronicAcids............................. 22 AldaricAcids............................ 22 CyclicAcetals............................ 24 Intramolecular Anhydrides . .................. 24 References . ............................ 25 2 Conformational Analysis of Monosaccharides ........... 27 Conformational Analysis of Acyclic Hydrocarbons . ........ 28 Conformational Analysis of Acyclic (Aldehydo) Forms of Monosaccharides . ....................... 31 xi xii Contents Conformational Analysis of Cyclic (Lactol, Hemiacetal) Forms of Monosaccharides ....................... 33 Furanoses . ............................ 33 Pyranoses . ............................ 36 Calculation of Conformational Energies of Pyranoses . ........ 41 References . ............................ 53 3 Anomeric Effect ............................ 57 Endo-anomeric Effect . ....................... 57 The Quantum-Mechanical Explanation . ............. 63 Exo-anomeric Effect . ....................... 67 Generalized Anomeric Effect . .................. 69 ReverseAnomericEffect...................... 72 AnomericEffectinSystemsO–C–N................ 84 References . ............................ 88 4 Isomerization of Sugars ........................ 95 Mutarotation.............................. 95 Anomerization............................. 105 Lobry de Bruyn–Alberda van Ekenstein Transformation . .... 108 References . ............................ 109 5 Relative Reactivity of Hydroxyl Groups in Monosaccharides ... 113 Introduction . ............................ 113 SelectiveAcylation(Esterification).................. 114 Selective p-Toluenesulfonylation (Tosylation) and Methanesulfonylation (Mesylation) . ............. 116 Selective Benzoylation . ....................... 120 SelectiveAcetylation........................ 127 Other Acylating Reagents ...................... 129 AcylMigrations........................... 133 Selective Alkylation and/or Arylation of Glycopyranosides . .... 136 Tritylation of Monosaccharides (Triphenylmethyl Ethers) . .... 136 Selective Benzylation of Monosaccharides ............. 137 Selective Alkylation of Metal Complexes of Monosaccharides . 138 References . ............................ 139 6 Cyclic Acetals and Ketals ....................... 143 Acetalation............................... 148 Benzylidenation ........................... 148 Ethylidenation ............................ 149 Ketalation................................ 150 Isopropylidenation (Acetonation) .................. 150 Transacetalation and Transketalation .................. 152 TheIsomerizationofCyclicAcetalsandKetals............ 154 TheMigrationofAcetalorKetalGroup.............. 155 Removal of Acetal and Ketal Groups ................. 157 Contents xiii Benzylidene Group . ....................... 157
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