Carbohydrate Chemistry Volume 25

388 Pages·1993·33.752 MB·English

by  R J Ferrier

Carbohydrate Chemistry
Volume 25

A Specialist Periodical Report
Ca r bo hy d rate C he m istr y
Monosaccharides, Disaccharides,
and Specific Oligosaccharides
Volume 25
A Review of the Recent Literature Published
during 1991
Senior Reporter
R. J. Ferrier,V ictoria University of Wellington, New Zealand
Reporters
R. Blattner, Industrial Research Limited, Lower Hutt, New Zealand
K. CIi nc h, Zeneca Ag roch emi cals, Brackn ell, Berks.
R. H. Furneaux, Industrial Research Limited, Lower Hutt,
New Zealand
P.C. Tyler, Industrial Research Limited, Lower Hutt, New Zealand
R. H. Wightman, Heriot- Watt University, Edinburgh
N. R. Williams, Birkbeck College, University of London
ROYAL
,SOCIETY OF
CHE h.1 I ST RY
ISBN 0-85186-692- 1
ISSN 0951-8428
0
The Royal Society of Chemistry, 1993
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., Newcastle upon Tyne
Preface
The completion of Volume 25 of this annual series, which covers the relevant literature
of 1991, obviously marks a milestone at which it is perhaps worthwhile emphasizing the
marked changes which the quarter century has seen in the organic chemistry of the
monosaccharides and related compounds. Throughout, a fairly consistent screening
policy has been used and retrieved 765 papers for abstracting in 1967 (Volume l), 1023
in 1978 and 2022 in 1990, the increase in activity being ascribable to concurrent enhanced
appreciation of the significance of sugars in biology and in general synthetic organic
chemistry on the one hand, and advances in separation and analytical techniques on the
other.
Much more significant than the simple number of papers cited is, in my
judgement, the striking changes in the quality of content of very many publications in the
field. A glance at Volume 1 shows that few papers published in 1967, for example, made
penetrating or seminal advances to knowledge, and from the point of view of the
Specialist Periodical Reporter all material was readily managed. Today’s literature is
vastly more complex, and it is rather difficult to do justice to many published papers in
a few sentences. Much of their content is very complex, it may be difficult to assign to
appropriate Chapters, and even the issue of relevance as a whole may be uncertain. Is
a particular paper on cyclitols or antibiotics or synthesis or analysis inside our guidelines
for cover? In which of perhaps six possible chapters is a complex report covered? When
does nucleoside chemistry become heterocyclic or nucleic acid chemistry? How much of
a 20-step synthesis which uses a sugar as key starting material for the preparation of a
complex macrocyclic antibiotic is relevant? The 25th milestone has taken on millstone
characteristics.
From their prejudiced point of view the reporters themselves use the Reports a
great deal in their research, and have growing experience of how valuable they are for
basic searches - even in these days of automated facilities. They trust others share this
sense of value of the Reports and note how readily they assist the identification of growth
areas and selective advances in the field. Progress is far from even.
Our writing team has been stable for several years, but now Dr Keith Clinch has
joined us as a welcome colleague from private industry, and we will be expanding further
for the next volume. Needless to say an enlarged team implies increased chances of one
member being held up by other responsibilities and thereby delaying production, but we
remain (still) of the view that we can reduce delays in publication and we continue to try.
It is probable that this volume will be the last in which Dr Neil Williams’
invaluable contribution as molecular structure producer will be required. Progress
dictates that computer art work be used in future, and while this will obviously be
welcome in one way, loss of Neil’s carbohydrate expertise in the handling of drawings will
be a considerable handicap to all Reporters. I acknowledge with warmest thanks his
major contributions as reporter, Senior Reporter and draughtsman over 17 years, and
look forward to his continuing assistance in the first of these roles.
Warm thanks go to all reporters for their patient assistance and to Dr P.G.
Gardam and Mr A.G. Cubitt of the Royal Society of Chemistry for their support.
R.J. Ferrier
April 1993
Contents
Chapter 1 Introduction and General Aspects 1
3
Chapter 2 Free sugars
1 Theoretical Aspects 3
2 Synthesis 3
Trioses-Hexoses 4
Chain-extended Compounds 5
3 Physical Measurements 9
4 Isomerisation 10
5 Oxidat ion 10
6 Other Aspects 11
References 12
Chapter 3 Glycosides 15
1 0-Glycosides 15
Synthesis of Monosaccharide Glycosides 15
Synthesis of Glycosylated Natural Products 25
0-Glycosides Isolated from Natural Products 29
Synthesis of Disaccharides and their
Derivatives 31
Hydrolysis and Other Reactions and Features 47
2 S-Glycosides 48
3 C-Glycosides 49
Pyranoid Compounds 49
Furanoid Compounds 56
References 58
Chapter 4 Oligosaccharides 64
1 General 64
2 Trisaccharides 65
Linear Homotrisaccharides 65
Linear Heterotrisaccharides 66
Branched Homotrisaccharides 68
Branched Heterotrisaccharides 68
...
Vlll Carbohydrate Chemistry
3 Tetrasaccharides 68
Linear Homotetrasaccharides 68
Linear Heterotetrasaccharides 68
Branched Homotetrasaccharides 69
4 Pentasaccharides 69
Linear Pentasaccharides 69
Branched Pentasaccharides 70
5 Hexasaccharides 70
Linear Hexasaccharides 71
Branched Hexasaccharides 71
Heptasaccharides 72
Higher Saccharides 73
Cyclodextrins 74
References 76
Chapter 5 Ethers and Anhydro-sugars 79
1 Ethers 79
Methyl Ethers 79
Other Alkyl and Aryl Ethers 80
2 Intramolecular Ethers (Anhydro-sugars) 81
Oxirans 81
Other Anhydrides 81
References 83
Chapter 6 Ace ta 1s 85
References 86
Chapter 7 Esters 87
1 Carboxylic Esters 87
Synthesis and Reactions 87
Isolation from Natural Sources 91
Phosphates and Related Esters 92
Sulfonates 96
Other Esters 98
References 101
Chapter 8 Halogeno-sugars 104
1 Fluoro-sugars 104
2 Chloro-, Bromo-, and Iodo-sugars 105
References 105