Rearrangements in the Course of Fluorination by Diethylaminosulfur Trifluoride at C-2 of Glycopyranosides: Some New Para

Reaction of a series of 21 glycosides unprotected at O-2 and featuring various configurations with DAST (diethylaminosulfur trifluoride) was monitored by 19F NMR spectroscopy. By means of the diacritical set of data (shift values and coupling constants) t

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Springer-Verlag Wien GmbH

Prof. Dr. Walther Schmid Institute of Organic Chemistry, University ofVienna, Vienna, Austria

Prof. Dr. Amold E. Stiitz Institute of Organic Chemistry, Technical University of Graz, Graz, Austria

This work is subject to copyright. AlI rights are reserved, whether the whole or part of the material is concemed, specificalIy those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machines or similar means, and storage in data banks. Product Liability: The publisher can give no guarantee for aH the information contained in this book. This does also refer to information about drug dosage and application thereof. In every individual case the respective user must check its accuracy by consulting other pharmaceutical literature. The use of registered names, trademarks, 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. © 2002 Springer-Verlag Wien Originally published by Springer-Verlag Wien New York in 2002 Softcover reprint of the hardcover 1st edition 2002

Cover illustration: M. Walter and T. K. Lindhorst, "Reactivity ... ", Fig. 2, page 126, this volume Typesetting: Thomson Press (India) Ltd., New Delhi Printed on acid-free and chlorine-free bleached paper SPIN: 10861929 With numerous Figures and Tables CIP data applied for

Special Edition of Monatshiflefiir ChemielChemica! Monthly VoI. 133, No. 4, 2002

ISBN 978-3-7091-7289-6 ISBN 978-3-7091-6130-2 (eBook) DOI 10.1007/978-3-7091-6130-2

Editorial Accompanying the rapid increase of knowledge on the extreme importance and vital roles of carbohydrates in living systems, carbohydrate chemistry has made its way from a quite underrated area of natural products research right into the focus of modern organic and bioorganic chemistry within a quarter of a century. Just by flicking through the graphical abstracts of major journals, large numbers of papers on carbohydrate chemistry can be found almost anywhere in the contemporary literature. The complexity and polyfunctionality of carbohydrates as a testing ground for modern organic methodology, carbohydrates as building blocks, carbohydrate related mimetics of natural products as enzyme probes, diagnostics, and therapeutics, carbohydrates in material sciences, all these and many more exciting topics demonstrate this lasting boom in glycosciences. Not many other areas are as rich in complexity, subtle reactivity differences, unusual behaviour of compounds and, as a result, so full of challenges, surprises, and rewards. Consequently, it was a great pleasure to accept the proposal by the Managing Editor of the Austrian journal Chemical Monthly, Prof. Heinz Falk, to compile a representative survey of timely research contributed by international leaders in the field as well as by outstanding young talents. This collection is intended to give evidence for the statements made above as well as to provide informat