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

10. Patented Literature 2616 10.1. Esterification 2616 10.2. Ether Formation 2619 10.2.1. Etherification without Cyclization 2619 10.2.2. Etherification with Cyclization 2624 10.3. N-Alkylation 2625 10.4. Other Reactions 2627 11. Summary and Outlook 2628 12. Note Added in Proof 2628 13. Abbreviations Used in This Review 2629 14. Acknowledgments 2629 15. Supporting Information Available 2630 16. References 2630

Mitsunobu and Related Reactions: Advances and Applications

BINOL: A Versatile Chiral Reagent

The application of the B-component lipase from the yeast Candida antarctica in organic synthesis is reviewed. This enzyme has been found to be a particularly efficient and robust lipase catalyzing a surprising diversity of reactions including many different regio- and enantio-selec-tive syntheses. Furthermore, the C. antarctica B-lipase is an example of an enzyme for which its specificity has been predicted based on the crystal structure and modeling of the active site region. This prediction is compared to experimental observations and a very close correlation is found.

One Biocatalyst–Many Applications: The Use of Candida Antarctica B-Lipase in Organic Synthesis

https://mmbr.asm.org/content/mmbr/57/3/655.full.pdf

Genetics of lipopolysaccharide biosynthesis in enteric bacteria.

Synthesis of methyl 2,3-dideoxy-DL-alk-2-enopyranosides from furan compounds

Synthesis of alkyl 4,6-di-o-acetyl-2,3-dideoxy-α-d-threo-hex-2- enopyranosides from 3,4,6-tri-o-acetyl-1,5-anhydro-2-deoxy- d-lyxo-hex-1-enitol (3,4,6-tri-o-acetyl-d-galactal)

New syntheses of d- and l-glycero-d-manno-heptoses

Publisher Summary This chapter describes the syntheses of sugar-type compounds containing four or more carbon atoms, an aldehyde or a ketone group, and a minimum of two hydroxyl groups (or their equivalents, such as amino or thiol groups) with at least one of them being bound to a center of chirality. Among the variety of noncarbohydrate precursors, acetylenes and alkenes have found wide application as substrates for the synthesis of monosaccharides. The parent compounds of all pyranoses—the 2H - and 4H -pyrans—and their derivatives are impractical as substrates for the synthesis of sugars. The formation of furan derivatives in acid-catalyzed dehydrations of carbohydrate substrates is a well known reaction. 1,2-Ethenediyl carbonate (1,3-dioxol-2-one; vinylene carbonate) is a readily available, versatile synthon having pronounced dienophilic properties. For the synthesis of optically active sugars, a number of natural compounds have been successfully employed. The syntheses of sugars described in this chapter demonstrate the general utility of starting materials employed as the precursors of various sugars of desired structure.

Aleksander Zamojski

Papers

Synthesis of methyl 2,3-dideoxy-DL-alk-2-enopyranosides from furan compounds

Synthesis of alkyl 4,6-di-o-acetyl-2,3-dideoxy-α-d-threo-hex-2- enopyranosides from 3,4,6-tri-o-acetyl-1,5-anhydro-2-deoxy- d-lyxo-hex-1-enitol (3,4,6-tri-o-acetyl-d-galactal)

New syntheses of d- and l-glycero-d-manno-heptoses

The Synthesis of Sugars from Non-Carbohydrate Substrates

The acid-catalysed reaction of thiols with alkyl 2,3-dideoxy-glyc-2-enopyranosides or glycals