Modern Organocatalyzed Methods in Carbohydrate Chemistry
This brief presents a valuable and concise overview of organocatalytic methodologies in carbohydrate chemistry. It includes glycosylation processes with de novo syntheses of carbohydrates and chain elongation of carbohydrates. The author, an academic of i
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Rainer Mahrwald
Modern Organocatalyzed Methods in Carbohydrate Chemistry 123
SpringerBriefs in Molecular Science
More information about this series at http://www.springer.com/series/8898
Rainer Mahrwald
Modern Organocatalyzed Methods in Carbohydrate Chemistry
123
Rainer Mahrwald Department of Chemistry Humboldt University Berlin Germany
ISSN 2191-5407 ISSN 2191-5415 (electronic) SpringerBriefs in Molecular Science ISBN 978-3-319-17592-8 ISBN 978-3-319-17593-5 (eBook) DOI 10.1007/978-3-319-17593-5 Library of Congress Control Number: 2015937737 Springer Cham Heidelberg New York Dordrecht London © The Author(s) 2015 This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. The publisher, the authors and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained herein or for any errors or omissions that may have been made. Printed on acid-free paper Springer International Publishing AG Switzerland is part of Springer Science+Business Media (www.springer.com)
Contents
1
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
1
2
Total Synthesis of Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . .
7
3
Organocatalyzed Cascade Reaction in Carbohydrate Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
35
Organocatalyzed Glycosylation Reactions of Carbohydrates . . . . .
67
4
v
Chapter 1
Introduction
This review intends to call the reader’s attention to the power of the carbonyl function of carbohydrates in several important transformations. The exhaustive utilization of this functionality has been made possible by the strong and aggressive development of organocatalysis. Several important reactions and methods have been established under the aura of organocatalysis, such as glycosylation, cascade reactions and total syntheses of carbohydrates. Besides that several other organocatalyzed methods have been elaborated in carbohydrate chemistry, e.g. organocatalyzed introduction of protective groups (for highly selective O-arylidenation of carbohydrates see [1], for selective acylation of carbohydrates see [2–6]). These methods th
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