Ca r bo hyd rate C he m ist ry Volume 32 A Specialist Periodical Report Carbohydrate Chemistry Monosaccharides, Disaccha rides and Specific Oligosaccharides Volume 32 A Review of the Literature Published during 1998 Senior Reporter R.J . Ferrier, Industrial Research Limited, Lower Hutt, New Zealand Rep0 rte rs R. Blattner, Industrial Research Limited, Lower Hutt, New Zealand K. Clinch, Industrial Research Limited, Lower Hutt, New Zealand R.A. Field, University of St.Andrews, St.Andrews, UK R.H. Furneaux, Industrial Research Limited, Lower Hutt, New Zealand J.M. Gardiner, UMlST, Manchester, UK K.RR. Kartha, University of St.Andrews, St.Andrews, UK D.M.G. Tilbrook, University of Western Australia, Nedlands, Australia F?C.T yler, Industrial Research Limited, Lower Hutt, New Zealand R.H. Wightman, Heriot Watt University, Edinburgh, UK RSmC ROYAL SOCIETY Of CHEMISTRY ISBN 0-85404-228-8 ISSN 095 1-8428 A catalogue record of this book is available from the British Library 0T he Royal Society of Chemistry 2001 All Rights Reserved Apart from any fair dealing for the purposes of research or private study, or criticism or review as permitted under the terms of the UK Copyright, Designs and Patents Act, 1988, this publication may not be reproduced, stored or trunsmitted, in any form or by any means, without the prior permission in writing of The Royal Society of Chemistry, or in the case of reprographic reproduction only in accordance with the terms of the licences issued by the Copyright Licensing Agency in the UK, or in accordance with the terms of the licences issued by the appropriate Reproduction Rights Organization outside the UK. Enquiries concerning reproduction outside the terms stated here should be sent to The Royal Society of Chemistry ut the address printed on this page. Published by The Royal Society of Chemistry Thomas Graham House, Science Park, Milton Road, Cambridge CB4 OWF, UK Registered Charity Number 207890 For further information see our web site at www.rsc.org Typeset by Computape (Pickering) Ltd, Pickering, North Yorkshire, UK Printed by Athenaeum Press Ltd, Gatehead, Tyne and Wear, UK Happily, for this Volume, we hope to have been able to return roughly to our normal production schedule and to have avoided the undue delay in publica- tion of Volume 31 which was brought about by the inordinate pressure under which one of our team had to operate. Fortunately this was temporary, but it did highlight the complexity of the task of bringing together the work of extremely busy people and our complete dependence on each one. Another factor on which we rely heavily is modern communication without which a group as geographically dispersed as ours could not function. The addition to the reporting team of Rob Field and Ravi Kartha, University of St. Andrews, and Matthew Tilbrook, University of Western Australia, has helped with the abstracting and writing tasks appreciably, and I am indebted to them for their cooperation and contributions. Keith Clinch has completed his role as Reporter which he has held since Volume 25, and I very readily record my gratitude to him. As a team we are concerned at how little the structure of our presentation has changed over the years while the subject has undergone revolution - particularly through the birth of glycobiology - and we are conscious of the need to adapt. We will try to do this, but must find means of limiting and defining the range of the subject material that is covered. Already this is becoming increasingly problematical with the limits extremely difficult to identify in newer topics such as dendrimer and combinatorial chemistry as well as in such traditional areas as cyclitol and nucleoside work. R.J. Ferrier June 2000 Contents Chapter 1 Introduction and General Aspects 1 References 2 Chapter 2 Sugars 3 Free 1 Theoretical Aspects 3 2 Synthesis 3 2.1 Tetroses to Hexoses 3 2.2 Chain-extended Sugars 6 3 Physical Measurements 10 4 Isomerization 10 5 Oxidation 11 6 Other Aspects 11 References 12 Chapter 3 Glycosides and Disaccharide 15 1 0-Glycosides 15 1.1 Synthesis of Monosaccharide Glycosides 15 1.2 Synthesis of Glycosylated Natural Products and Their Analogues 25 1.3 0-GlycosidFs Isolated from Natural Products 28 1.4 Synthesis of Disaccharides and Their Derivatives 28 1.5 Disaccharides with Anomalous Linking or Containing Modified Rings 34 1.6 Reactions, Complexation and Other Features of 0-Glycosides 35 2 S-, Se- and Te-Glycosides 35 - Carbohydrate Chemistry, Volume 32 0T he Royal Society of Chemistry, 2001 vii ... Vlll Cont ents 3 C-Glycosides 37 3.1 Pyranoid Compounds 37 3.2 Furanoid Compounds 45 References 46 Chapter 4 Oligosaccharides 58 General 58 Trisaccharides 59 2.1 General 59 2.2 Linear Homotrisaccharides 59 2.3 Linear Hetero trisaccharides 60 2.4 Branched Homot risaccharides 62 2.5 Branched Heterotrisaccharides 62 2.6 Analogues of Trisaccharides and Compounds with Anomalous Linking 62 Tet rasacch arides 63 3.1 Linear Homotetrasaccharides 63 3.2 Linear Heterotetrasaccharides 64 3.3 Branched Heterotetrasaccharides 64 3.4 Analogues of Tetrasaccharides and Compounds with Anomalous Linking 66 Pentasaccharides 67 4.1 Linear Homopentasaccharides 67 4.2 Linear Heteropentasaccharides 67 4.3 Branched Homopentasaccharides 68 4.4 Branched Heteropentasaccharides 68 4.5 Pentasaccharides with Anomalous Linking 68 Hexasaccharides 68 5.1 Linear Hexasaccharides 68 5.2 Branched Hexasaccharides 69 5.3 Hexasaccharides with Anomalous Linking 70 Heptasaccharides 71 Octasaccharides 72 Nonasaccharides 72 Higher Saccharides 73