Carbohydrate Chemistry Volume 29

460 Pages·1997·32.027 MB·English

Carbohydrate Chemistry
Volume
29

A Specialist Periodical Report
Ca rb oh yd rate Ch e m ist ry
Monosaccharides, Disaccharides
and Specific Oligosaccharides
Volume 29
A Review of the Literature Published during 1995
Senior Reporter
R. J. Ferrier, Wctoria 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
J. M. Gardiner, UMIST, Manchestec UK
P. C. Tyler, Industrial Research Limited, Lower Hutt, New Zealand
R. H. Wightman, Heriot Watt Universiv, Edinburgh, UK
THE ROYAL
SOCIETY OF
C HE M I ST RY
Information
Services
ISBN 0-8 5404-2
13-X
ISSN 0951-8428
0T he Royal Society of Chemistry 1997
All rights reserved.
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Preface
The old order has indeed changed, and beginning with this volume, each member
of the abstractindwriting team has been contracted to produce chapters of
agreed maximum lengths. In consequence, it has been necessary to compress
some abstracting and reporting yet further, so that in many instances the main
objective has been to call attention to original work and indicate its source rather
than to provide a meaningful summary from which the interested reader could
work. The reporters are acutely aware that brief notes do scant justice to
developing literature of ever-increasing complexity.
More and more carbohydrate research is being developed and stimulated by
chemists who are not specialized in the field - and the subject is being greatly
enhanced in consequence - and more and more it is merging with organic
chemistry generally. Increasingly, important new work is appearing in non-
specialized journals, the first 3 issues of Journal of Organic Chemistry for 1996 for
example each containing about 10 papers to be cited in Specialist Periodical
Reports, Carbohydrate Chemistry.
This year’s volume has been produced by a depleted team and the members are
due major thanks for taking on additional work under particularly frustrating
circumstances.
Mrs Janet Freshwater and Mr Alan Cubitt, The Royal Society of Chemistry,
are thanked most warmly for the cooperation and help they have provided.
R.J. Ferrier
May, 1997
V

Cont ents
Chapter 1 Introduction and General Aspects 1
Chapter 2 Free Sugars 3
1 Theoretical Aspects 3
2 Synthesis 3
2.1 Tetroses and Pentoses 4
2.2 Hexoses 5
2.3 Chain-extended Sugars 6
3 Physical Measurements 11
4 Isomerization 11
5 Oxidation 11
6 Other Aspects 12
References 13
Chapter 3 Glycosides and Dmccharides 16
1 0-Glycosides 16
1.1 Synthesiso f Monosaccharide Glycosides 16
1.2 Synthesiso f Glycosylated Natural Products 21
1.3 0-Glycosides Isolated from Natural Products 25
1.4 Synthesiso f Disaccharides and their Derivatives 25
1.5 Disaccharidesw ith Anomalous Linking 35
1.6 Reactions, Intermolecular Complexation and other
Features of Glycosides 36
2 S-a nd Se-Glycosides 38
3 C-GI ycosides 41
3.1 Pyranoid Compounds 41
3.2 Furanoid Compounds 52
References 53
vii
viii Contents
Chapter 4 Oligosaccharides 63
1 General 63
2 Trisaccharides 65
2.1 Linear Homotrisaccharides 66
2.2 Linear Heterotrisaccharides 67
2.3 Branched Homotrisaccharides 68
2.4 Branched Heterotrisaccharides 68
2.5 Analogues of Trisaccharides 69
3 Tetrasaccharides 70
3.1 Linear Homotetrasaccharides 71
3.2 Linear Heterotetrasaccharides 72
3.3 Branched Homotetrasaccharides 72
3.4 Branched Heterotetrasaccharides 72
3.5 Trisaccharide Analogues 73
4 Pentasaccharides 74
4.1 Linear Pentasaccharides 74
4.2 Branched Pentasaccharides 75
4.3 Pentasaccharide Analogues 76
5 Hexasaccharides 76
5.1 Linear Hexasaccharides 76
5.2 Branched Hexasaccharides 77
6 Heptasaccharides 78
7 Octasaccharides 78
8 Nonasaccharides 78
9 Higher Saccharides 79
10 Cyclodextrins 80
References 83
Chapter 5 Ethers and Anhydro-sugars 91
1 Ethers 91
1.1 Methyl Ethers 91
1.2 Other Alkyl and Aryl Ethers 91
2 Intramolecular Ethers (Anhydro-sugars) 94
2.1 Oxirans 94
2.2 Other Anhydrides 96
References 96