Carbohydrate Chemistry Volume 27

414 Pages·1995·20.519 MB·English

Carbohydrate Chemistry
Volume 27

A Specialist Periodical Report
Ca rbo hyd rate C hem istr y
Monosaccharides, Disaccha rides,
a nd Specific 0I i g osacc ha rides
Volume 27
A Review of the Literature Published
during 1993
Senior Reporter
R. J. Ferrier, Victoria University of Wellington, New Zealand
Reporters
R. Blattner, Industrial Research Limited, Lower Hutt, New Zealand
K. Clinch, Industrial Research Limited, Lower Hutt, New Zealand
R. H. Furneaux, Industrial Research Limited, Lower Hutt,
New Zealand
T. C. Gallagher, University of Bristol
P. C. Tyler, Industrial Research Limited, Lower Hun, New Zealand
R. H. Wightman, Heriot- Watt University, Edinburgh
N. R. Williams, Birkbeck College, University of London
SOCIETY OF
CH EM IS TRY
ISBN 0-85404-203-2
ISSN 095 1-8428
0 The Royal Society of Chemistry, 1995
All rights reserved.
Apart from uny 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
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prior permission in writina of The Royal Society of
Chemistry, or in the case of reprographic reproduction
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Chemistry at the address printed on this page.
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
In Prefaces to previous Volumes I have commented on the increasing activity in the field
of carbohydrate chemistry and also on the increasing complexity of many current research papers.
With these continuing trends the need for Reporters to this Series to abstract more selectively is
growing, and the chapter writers also have to abstract the first synopses ever more severely
because we must work within space-determined limits. The density of data in succeeding
Volumes is therefore increasing rather rapidly as is illustrated by the observation that Volumes
16 and 26 (1 982 and 1992 literature) contained 13 and 3 1 pages of author indexes, respectively,
while the overall page numbers only increased by 25%. The rather severe distillation processes
now required inevitably increase the chances of imprecision - not least as far as impressions given
of papers are concerned - and we can visualise authors' views of our maltreatments when their
masterpieces are dismissed in a line or so. Readers should be aware of this severe limitation in
our methods and are advised to consult primary sources as appropriate.
A notable feature this year has been the increase in the number of ingenious developments
from which far-reaching consequences could come, and while this is illustrated in several
Chapters, the topic of glycosidation procedures illustrates it particularly well. To be able to
"switch on" one glycosylating agent in the presence of another (for example, phenylseleno
compounds in the presence of phenylthio analogues), to incorporate a concurrent 2-deoxy
generating step into a glycosylation reaction and to synthesize a trisaccharide from its constituents
in selective one-pot reactions are indeed ingenious. The number of "smart" developments is on
the increase!
As the boundaries of the subject expand more choices have to be made in determining
which research papers should be abstracted. This year, it seems the following question has
emerged: should papers on the syntheses of "marginal carbohydrates" e.g. acyclic nucleosides,
cyclitols, deoxynojirimycin be abstracted when non-carbohydrates are the starting materials used?
Yet another guideline will be required.
This Volume sees the last contributions by Tim Gallagher, and I thank him warmly for his
work on some of the more demanding parts of the writing task. For their work and cooperation
the staff of the Royal Society of Chemistry - especially Mr A G Cubitt and his artwork colleagues
- are also thanked sincerely.
R J Ferrier
May 1995

Contents
Chapter 1 Introduction and General Aspects 1
Chapter 2 Free Sugars 3
1 Theoretical Aspects 3
2 Synthesis 3
2.1 Trioses to Hexoses 3
2.2 Chain-extended Compounds 5
3 Physical Measurements 9
4 Isomerization 10
5 Oxidation 10
6 Other Aspects 11
References 11
Chapter 3 Glycosides and Disaccharides 14
1 0-G1y cosides 14
1.1 Synthesis of Monosaccharide Glycosides 14
1.2 Synthesis of Glycosylated Natural Products 19
1.3 0-Glycosides Isolated from Natural Products 23
1.4 Synthesis of Disaccharides and their Derivatives 25
1.5 Hydrolysis and Other Features of Glycosides and 38
Disaccharides
2 S- and Se-Glycosides 39
3 C-Gl ycosides 42
3.1 Pyranoid Compounds 42
3.2 Furanoid Compounds 51
References 52
...
Carbohydrate Chemisrry
Vlll
Chapter 4 Oligosaccharides 58
1 General 58
2 Trisaccharides 59
2.1 Linear Homotrisaccharides 59
2.2 Linear Heterotrisaccharides 59
2.3 Branched Homotrisaccharides 63
2.4 Branched Heterotrisaccharides 64
2.5 Analogues of Trisaccharides 65
3 Tetrasaccharides 65
3,l Linear Homotetrasaccharides 65
3.2 Linear Heterotetrasaccharides 66
3.3 Branched Homotetrasaccharides 67
3.4 Branched Heterotetrasaccharides 67
3.5 Tetrasaccharide Analogues 67
4 Pentasaccharides 68
4.1 Linear Pentasaccharides 68
4.2 Branched Pentasaccharides 69
5 Hexasaccharides 69
5.1 Branched Hexasaccharides 69
6 Heptasaccharides 71
7 Octasaccharides 72
8 Higher Saccharides 72
9 Cyclodextrins 72
References 75
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 81
2 Intramolecular Ethers (Anhydro-sugars) 81
2.1 Oxirans 81
2.2 Other Anhydrides 82
References 84