Publisher Summary This chapter provides an overview of the 13 Carbon-nuclear magnetic resonance ( 13 C-NMR) spectroscopy of monosaccharides. The 13 C-NMR spectroscopy has become increasingly important as a tool for the characterization and structural elucidation of sugars and their derivatives. Although 13 C-NMR is closely related to 1 H-NMR spectroscopy, especially when both types of spectra are recorded with Fourier-transform instruments, the two techniques are sufficiently different to be valuable complements to each other. In many cases, in particular when dealing with complex molecules such as polysaccharides, the amount of information obtainable from 1 H-NMR spectra is limited as compared to that revealed by 13 C- NMR spectra. This chapter provides an almost complete collection of 13 C- NMR chemical shifts of monosaccharides, their methyl glycosides, and acetates, along with the examples of shift data for as many different types of monosaccharide derivative as possible. It also provides details on sampling techniques and assignment techniques, and discusses the identity of monosaccharides, their structure determination, and conformational analysis .

Carbon-13 Nuclear Magnetic Resonance Spectroscopy of Monosaccharides

Metabolite profiling by one- and two-dimensional NMR analysis of complex mixtures

Publisher Summary This chapter presents a compilation of 13 C-nuclear magnetic resonance (NMR) data for oligosaccharides in the form of tables. The literature-survey presented in the chapter covers most of the data of 1982, and all of the information given had been measured for solutions in D 2 O unless stated otherwise. The data for peracetates of xylobioses and of glucobioses were recorded for solutions in CDCl 3 . All data have been copied from the original articles. For mutarotated mixtures of trisaccharides and larger oligosaccharides, the complete set of data is given for the α anomer, but only the chemical shifts for the reducing end of the anomer are given, provided that all other chemical shifts (for the remaining units) are identical. The sampling and assignment techniques used for the measurement of 13 C-NMR spectra of oligosaccharides are identical to those for monosaccharides. Particularly for oligosaccharides, it is important to measure the spectra at the same temperature—that is, with a precision better than ±0.5 p.p.m., when data are to be compared accurately.

Carbon-13 nuclear magnetic resonance data for oligosaccharides

Considerable problems attend the synthesis of biologically important natural products whose carbohydrate components display a greater or lesser degree of complexity. The present progress report surveys recent developments in the formation of O-glycosidic bonds starting from 1-halo sugars and from sugar 1,2-orthoesters. Particular emphasis is placed on attempts to reach a better understanding of the steric course of glycosylation reactions on the basis of mechanistic considerations. Studies on the silver-salt dependence of the Koenigs-Knorr synthesis led to improvements in preparative applications and to new concepts concerning the reaction course. The introduction of sugar 1,2-orthoesters as glycosylation components has greatly enriched our preparative armoury for the synthesis of trans glycosides. Remarkable progress has also been made in the synthesis of cis glycosides, in part by exploiting novel neighbouring group effects.

Results and Problems of O-Glycoside Synthesis

Philippe J.A. Vottero

Papers

Effets de substituants sur les déplacements chimiques en r.m.n.-13C pour la série du d-xylose

Synthesis of Benzylated Cycloisomaltotri‐ and ‐hexaoside

Nucleophilic opening of bis-epoxides: a new access to symmetrically functionalised macrocycles

Synthèse d'oligosaccharides sur polymère support

Synthesis of benzylated cycloisomaltotetraose.