Carbohydrate-spiro-heterocycles (Topics in Heterocyclic Chemistry Book 57)

This volume is devoted to compounds in which the spiro centre is part of a pyranoid or furanoid or an iminosugar ring. The chapters contributed deal with methodological peculiarities of syntheses of natural and artificial sugar derived spirocycles as well as their biological applications and other utilities including marketed drugs. Carbohydrates are ubiquitous molecules in nature and participate in a vast number of biological interactions. Especially their conjugates with practically all kinds of primary and secondary metabolic small molecules (and also biomacromolecules) representing valuable tools for glycobiology research and also lead compounds for drug discovery. While monosaccharides per se appear as heterocycles, their natural conjugates frequently exhibit spiro(hetero)cyclic derivatives, in many cases of high therapeutical relevance. As a consequence, the field of carbohydrate-spiro-heterocycles attracts intense interest from both chemical and biomedical aspects therefore this volume will be of interest for synthetic and medicinal chemists and (glyco)biologists, as well as researchers involved in various biomedical fields. Front Matter ....Pages i-vii Anomeric Spiro-Annulated Glycopyranosides: An Overview of Synthetic Methodologies and Biological Applications (Maxime Pommier, Sébastien Vidal)....Pages 1-25 Cycloaddition Reactions of Sugar-Based Olefins, Nitrones and Nitrile Oxides: En Route to Saccharidic Spiroisoxazoli(di)nes (Nadia Pellegrini-Moïse, Mylène Richard)....Pages 27-49 Carbohydrate Spiro-heterocycles via Radical Chemistry (Angeles Martín, Ernesto Suárez)....Pages 51-104 Carbohydrate-Derived Spiroketals and Spirocyclic Lactones (Perali Ramu Sridhar)....Pages 105-136 Cyanohydrins and Aminocyanides as Key Intermediates to Various Spiroheterocyclic Sugars (Solen Josse, Denis Postel)....Pages 137-169 Recent Advances in the Chemistry and Biology of Spirocyclic Nucleosides (Martín Soto, Humberto Rodríguez-Solla, Raquel Soengas)....Pages 171-213 Spiroketal Phthalane C-Glycosides: Synthesis of Papulacandins and SGLT2 Inhibitors (Yoshihiko Yamamoto)....Pages 215-260 Spiro Iminosugars: Structural Diversity and Synthetic Strategies (Damien Hazelard, Raphaël Hensienne, Jean-Bernard Behr, Philippe Compain)....Pages 261-290 Back Matter ....Pages 291-295