Carbohydrate chemistry : monosaccharides, disaccharides, and specific oligosaccharides, A review of the literature published in 1992

376 Pages·1994·27.472 MB·English

by  Robert J Ferrier, Royal Society of Chemistry

Carbohydrate Chem istr y
Volume 26

A Specialist Periodical Report
Carbohydrate Chemistry
Monosaccharides, Disacchar ides,
and Specific 0 Ii go sacc ha rides
Volume 26
A Review of the Literature Published
during 1992
Senior Reporter
R. J. Ferrier, Victoria University of Wellington, New Zealand
Reporters
R. Blattner, Industrial Research Limited, Lower Hutt, New Zealand
Clinch, Zeneca Agrochemicals, Bracknell, Berks.
K.
R. H. Furneaux, Industrial Research Limited, Lower Hutt,
New Zealand
T. C. Gallagher, University of Bristol
P. C. Tyler, Industrial Research Limited, Lower Hutt, New Zealand
R. H. Wightman, Heriot- Watt University, Edinburgh
V..R. Williams, Birkbeck College, University of London
HE M I STRY
C
ISBN 0-85 186-991 -2
ISSN 0951-8428
OThe Royal Society of Chemistry, 1994
All Rights Reserved
No part of this book may be reproduced or transmitted in any form
or by any means-graphic, electronic, including photocopying, recording,
taping or information storage and retrieval systems-without
written permission from The Royal Society of Chemistry
Published by the Royal Society of Chemistry,
Thomas Graham House, Science Park, Cambridge CB4 4WF
Printed in Great Britain by
Athenaeum Press Ltd, Gateshead, Tyne & Wear.
Preface
The literature of 1992 again vividly illustrates the increasing complexity of the chemistry of the
smaller members of the carbohydrate family, and while this increases the difficulty of the
reporting task, it concurrently adds to the interest and benefit of the job from the reviewers'
point of view. No longer are members of our team confined to reading "standard" carbohydrate
chemistry; their duties introduce them to a vast range of reactions and 'methods which have
applicability in general organic chemistry, and many natural products other than sugars and a
range of biochemical phenomena must be surveyed in the course of abstracting.
One worrying issue directly related to the increasing complexity of the reactions now used
with carbohydrates relates to the abbreviations employed for ever-more-complex reagents and
substituent groups. Unhappily it is becoming not unusual for us to encounter
abbreviations/acronyms which are not even explained in the texts of papers, and in such cases
we must retain them in our abstracts, and thus be less helpful to readers than we would wish.
Our lists of abbreviations given at the beginning of each volume are therefore becoming
deficient, and this we of course regret. The time has come, one might speculate, for a
standardisation in the use of abbreviated names and for an approval system. Such
developments certainly would allow us to improve our product.
This volume sees the introduction of computer-drawn structural formulae. We trust that
the inevitable minor problems caused by the transition will resolve readily and that we will be
able to bring forward the publication dates. While this remains a continuing objective a
necessary increase in the size of the team brings with it increasing possibility of delays.
This year Dr Tim Gallager, University of Bristol, is welcomed as a reporter, and the help
of the staff of the Royal Society of Chemistry, especially Mr. A G. Cubitt and the artwork staff,
is acknowledged with warm thanks.
J Femer
R
April 1994

Contents
Chapter 1 Introduction and General 1
Aspects
Chapter 2 Sugars 3
Free
1 Theoretical Aspects 3
2 Synthesis 3
Trioses to Hexoses 3
Chain-extended Compounds 7
3 Physical Measurements 10
4 Isomerisation 11
5 Oxidation 11
6 Other Aspects 12
References 12
Chapter 3 Glycosides 15
1 O-Glycosides 15
1.1 Synthesis of Monosaccharide Glycosides 15
1.2 Synthesis of Glycosylated Natural Products 22
1.3 O-Glycosides Isolated from Natural Products 24
1.4 Synthesis of Disaccharides and their Derivatives 25
1.5 Hydrolysis and Other Features 38
2 S- and Se-Glycosides 40
3 C-Glycosides 43
3.1 Pyranoid Compounds 43
3.2 Furanoid Compounds 50
References 52
... Carbohydrate Chemistry
Vlll
Chapter 4 Oligosaccharides 59
1 General 59
Tris accharides 51
2
2,l Linear Homotrisaccharides 61
2.2 Linear Heterotrisaccharides 62
2.3 Branched Homotrisaccharides 63
Branched Heterotrisaccharides 63
2.4
2.5 Analogues of Trisaccharides 64
3 Tetrasaccharides 66
3.1 Linear Homotetrasaccharides 66
3.2 Linear Heterotetrasaccharides 66
Branched Homotetrasaccharides 67
3.3
Tetrasaccharide Analogues 67
3.4
4 Pentasaccharides 68
4.1 Linear Pentasaccharides 68
4.2 Branched Pentasaccharides 68
5 Hexasaccharides 68
5.1 Linear Hexasaccharides 69
5.2 Branched Hexasacchandes 69
Heptasaccharides 70
6
7 Octasaccharides 70
8 Higher Saccharides 71
9 Cy clodextrins 72
References 73
Chapter 5 Ethers and Anhydro-sugars 79
1 Ethers 79
1.1 Methyl Ethers 79
1.2 Other Alkyl and Aryl Ethers 79
1.3 Silyl Ethers 80
2 Intramolecular Ethers (Anhydro-sugars) 80
2.1 Oxirans 80
2.2 Other Anhydrides 81
References 82