Carbohydrate Chemistry: Volume 19 (Specialist Periodical Reports, Volume 19),Used

Excerpt. Reprinted by permission. All rights reserved. Carbohydrate Chemistry Volume 19Part I Monosaccharides, Disaccharides, and Specific OligosaccharidesBy N. R. WilliamsThe Royal Society of ChemistryCopyright 1987 The Royal Society of ChemistryAll rights reserved.ISBN: 9780851862224ContentsChapter 1 Introduction, 1, Chapter 2 Free Sugars, 3, Chapter 3 Glycosides and Disaccharides, 16, Chapter 4 Oligosaccharides, 38, Chapter 5 Ethers and Anhydrosugars, 48, Chapter 6 Acetals, 56, Chapter 7 Esters, 61, Chapter 8 Halogenosugars, 78, Chapter 9 Aminosugars, 85, Chapter 10 Miscellaneous Nitrogen Derivatives, 101, Chapter 11 Thio and Selenosugars, 117, Chapter 12 Deoxysugars, 121, Chapter 13 Unsaturated Derivatives, 129, Chapter 14 Branchedchain Sugars, 139, Chapter 15 Aldosuloses and Dialdoses, 148, Chapter 16 Sugar Acids and Lactones, 151, Chapter 17 Inorganic Derivatives, 159, Chapter 18 Alditols and Cyclitols, 165, Chapter 19 Antibiotics, 177, Chapter 20 Nucleosides, 194, Chapter 21 N.M.R. Spectroscopy and Confonational Features, 217, Chapter 22 Other Physical Methods, 228, Chapter 23 Separatory and Analytical Methods, 238, Chapter 24 Synthesis of Enantiomerically Pure Noncarbohydrate Compounds, 253, CHAPTER 1Introduction and General AspectsThe past year has seen a continued development of the research area covered in this report towards specific biological applications of mono and disaccharides, especially the synthesis of disaccharides and oligosaccharides which are increasingly sought as probes for investigating immunological interactions, and the synthesis of analogues of antibiotics and nucleosides in the search for more effective antibiotics and antimetabolites. Nevertheless, the contents of the other chapters clearly indicate that wider aspects of monosaccharide chemistry continue to excite the interest of carbohydrate chemists, and also others who find carbohydrates convenient chiral sources for a wide range of biological compounds. Modern techniques of n.m.r. spectroscopy and mass spectrometry are also proving of great benefit for the analysis of complex carbohydrate structures. The fact that we record over 1400 references contributed by nearly 3000 workers speaks for itself!Fringe areas have continued to pose a problem as to where to draw a line between carbohydrates and noncarbohydrate materials. In Chapter 4 we have concentrated on the synthesis of specific oligosaccharides, and the title of the report has been modified to reflect the distinction we wish to make between oligosaccharides occurring as such or attached to aglycones, which includes many antibiotics, and oligosaccharides recognized as structural units of polysaccharides. Likewise the coverage of other materials which are only part carbohydrate has been generally selective for those papers which discuss the chemistry of the carbohydrate moiety; obviously, distinctions are not always clear, and we hope that not too many papers get omitted which would be of interest to readers of this report.Papers of more general carbohydrate interest published this year have included a description of a computer programme for selecting protecting groups of alcohols, ketones, and alkenes, details of a new ballstick building set for sugars, and reviews (in Japanese) on the reaction of sugar derivatives with Grignard reagents (asymmetric reactions, acetal cleavage, deoxygenation of vicdiol monosulphonates, anomerization and ringopening of furanosides) and on the application of electrochemical oxidation and reduction of carbohydrates. A relationship has been established for several carbohydrates between the partial molar heat capacity and the number of equatorial hydroxy groups in aqueous solution; exceptionally large values are caused by specific interaction of equatorial hydroxy groups with water molecules.CHAPTER 2Free SugarsThe processing of hardwoods to produce xylitol and other polyols monosaccharides and furfural is the subject of a Russian re