Carbohydrate Chemistry Volume 33

476 Pages·34.725 MB·English

Carbohydrate Chemistry
Volume 33
SPECIALIST
PERIODICAL REPORTS
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A Specialist Periodical Report
Carbohydrate Chemistry
Monosaccharides, Disaccharides
and Specific Oligosaccharides
Volume 33
A Review of the Literature Published during 1999
Senior Reporter
R.J. Ferrier, Industria/ Research Limited, Lower Hutt,
New Zealand
Reporters
R. Blattner, 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, UMIST, Manchester, UK
J.O. Hoberg, Victoria University of Wellington, Wellington,
New Zea la n d
K.P.R. Kartha, University of St.Andrews, St.Andrews, UK
D.M.G. Tilbrook, University of Western Australia, Nedlands,
Australia
P.C. Tyler, Industrial Research Limited, Lower Hutt,
New Zealand
R.H. Wightman, Heriot- Watt University, Edinburgh, UK
RSeC
_ _
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ROYAL SOCIETY OF CHEMISTRY
ISBN 0-85404-233-4
ISSN 095 1-8428
A catalogue record of this book is available from the British Library
0T he Royal Society of Chemistry 2002
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Preface
Yet again our team has completed this volume well behind schedule, and is all
too aware of the inappropriate delay in reporting on the literature of our field
published in the last (or second last?) year of the millennium. Half of our
members are under undue work-related stress, and it is unreasonable to expect
them to continue in these circumstances especially with an ever-expanding
-
and increasingly complex job. Volume 34, covering the literature for the year
2000, may therefore be the last of the current series unless of course less
-
pressurized volunteers can be found to allow it to continue. It was interesting
to note at a recent meeting of Senior Reporters of the Specialist Periodical
Reports that I was alone in recording our need to call a halt, and I had to
wonder whether activity in carbohydrate science has recently been increasing
in a selective manner. Given the birth of glycobiology and the overdue wide
recognition of the sugars as substances with ‘real’ organic chemistry and also
with immense potential significance in pharmaceutical science, perhaps this is
not unexpected. Electronic searching methods are seemingly at the point of
largely replacing traditional abstractindreviewing hard copy procedures in the
field.
This volume describes much that follows logically from what has gone
before with heavy emphasis on the reporting of developing aspects of the
organic chemistry of the carbohydrates. However, as has been the case for
several years, the eye catching new work is specifically focused in the field
between chemistry and biology and medicine. Nowhere is this more apparent
than in the area of the synthesis of oligosaccharides and glycoconjugates of
importance in medicine where Danishefsky’s syntheses of cancer antigens
based on oligosaccharides and glycopeptides may have brought the future to
hand. With rapidly developing methods based, for example, on the use of
computer-selected reactants in one pot procedures, and intramolecular glyco-
sidic and specific enzymic couplings, we are surely at the threshold of the age
of the application of complex carbohydrates to specific medical problems.
How appropriate that the signs may also be pointing to the use of molecular
biological methods in the field of oligosaccharide synthesis.
John Gardiner, who has been responsible for writing the key and demanding
chapter on the use of carbohydrates in the synthesis of chiral non-carbohydrate
compounds, must hand over his responsibilities with this volume. His con-
tributions to the last six volumes are acknowledged with gratitude, and John
Hoberg is welcomed to the reporting team.
Janet Freshwater and Alan Cubitt have provided excellent liaison with the
vi Preface
Royal Society of Chemistry over several years, and their administrative and
practical help has been very much appreciated.
R. J. Ferrier
November 200 1
Contents
Chapter 1 Introduction and General Aspects 1
References 2
Chapter 2 Free Sugars 3
1 Theoretical Aspects 3
2 Synthesis 3
2.1 Tetroses and Pentoses 3
2.2 Hexoses 4
2.3 Chain-extended Sugars 6
3 Natural Products 12
4 Other Aspects 13
References 13
Chapter 3 Glycosides and Disaccharides 16
1 0-Glycosides 16
1.1 Synthesis of Monosaccharide Glycosides 16
1.2 Synthesis of Glycosylated Natural Products and
Their Analogues 24
1.3 0-Glycosides Isolated from Natural Products 27
1.4 Synthesis of Disaccharides and Their Derivatives 27
1.5 Disaccharides with Anomalous Linking 37
1.6 Reactions, Complexation and Other Features of
0-Glycosides 37
2 S-, Se- and Te-Glycosides 39
3 C-Glycosides 40
3.1 General 40
3.2 Pyranoid Compounds 40
3.3 Furanoid Compounds 49
References 51
Carbohydrate Chemistry, Volume 33
0T he Royal Society of Chemistry, 2002
vii
viii Con tents
Chapter 4 Oligosaccharides 62
1 General 62
2 Trisaccharides 63
2.1 General 63
2.2 Linear Homotrisaccharides 63
2.3 Linear Heterotrisaccharides 64
2.4 Branched Homotrisaccharides 68
2.5 Branched Heterotrisaccharides 68
2.6 Analogues of Trisaccharides and Compounds with
Anomalous Linking 68
3 Tetrasaccharides 69
3.1 Linear Homotetrasaccharides 69
3.2 Linear Heterotetrasaccharides 70
3.3 Branched Heterotetrasaccharides 71
3.4 Analogues of Tetrasaccharides and Compounds with
Anomalous Linking 71
4 Pentasaccharides 72
4.1 Linear Heteropentasaccharides 72
4.2 Branched Heteropentasaccharides 74
5 Hexasaccharides 75
5.1 Linear Homohexasaccharides 75
5.2 Linear Heterohexasaccharides 76
5.3 Branched Homohexasaccharides 77
5.4 Branched Heterohexasaccharides 77
6 Heptasaccharides 78
7 Octasaccharides 79
8 Higher Saccharides 80
9 Cyclodextrins 81
9.1 General Matters 81
9.2 Branched Cyclodextrins 81
9.3 Cyclodextrin Ethers 81
9.4 Cyclodextrin Esters 82
9.5 Amino Derivatives 82
9.6 Thio and Seleno Derivatives 83
9.7 Halogenated Derivatives 84
9.8 Deoxy Derivatives 84
9.9 Oxidized Derivatives 84
References 85