Selective glycosylations with furanosides

CAROLA GALLO -RODRIGUEZ; GUSTAVO A. KASHIWAGI

Selective Glycosylation - Synthetic Methods and Catalysts

Wiley-VCH Verlag GmbH

Lugar: Weinheim; Año: 2017; p. 297 - 326

Carbohydrates in the furanose form are ubiquitous in nature. In mammals, furanoses are only restricted to ribose as components of nucleic acids. Nevertheless, furanoses can be found in bacteria, fungi, protozoa and plants. The interest in the synthesis of furanose-containing oligosaccharides has been growing very fast in the last years because furanoses are often constituents of pathogenic microorganism. For example, synthetic oligosaccharides would provide tools for studying their metabolic pathway pursuing a chemotherapeutic agent, or a precise antigen epitope for immunological studies. Whereas the 1,2-trans glycosidic linkage is easily constructed by anchimeric assistance, the stereoselective synthesis of 1,2-cis furanosyl units constitutes one of the most challenging issues in oligosaccharide synthesis. The flexibility of the furanose ring providing a low anomeric effect compared to pyranoses increases the difficulty for the construction of theses linkages. The recent advances in the furanose glycosylation field will be discussed; its scope and limitation, including the use of conformationally restricted furanosyl donors