Selective glycosylations with furanosides

GUSTAVO A. KASHIWAGI; CAROLA GALLO-RODRIGUEZ

Selective Glycosylation - Synthetic Methods and Catalysts

Wiley-VCH Verlag GmbH & Co. KGaA

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

Selective glycosylations with furanosidesCarbohydrates inthe furanose form are ubiquitous in nature. In mammals, furanoses are onlyrestricted to ribose as components of nucleic acids. Nevertheless, furanosescan be found in bacteria, fungi, protozoa and plants. The interest in thesynthesis of furanose-containing oligosaccharides has been growing very fast inthe last years because furanoses are often constituents of pathogenicmicroorganism. For example, synthetic oligosaccharides would provide tools for studying theirmetabolic pathway pursuing a chemotherapeutic agent, or a precise antigenepitope for immunological studies.  Whereas the 1,2-trans glycosidic linkage is easily constructed by anchimericassistance, the stereoselective synthesis of 1,2-cis furanosyl units constitutes one of the most challenging issuesin oligosaccharide synthesis. The flexibility of the furanose ring providing a lowanomeric effect compared to pyranoses increases the difficulty for the constructionof theses linkages. The recent advances in the furanose glycosylation fieldwill be discussed; its scope and limitation, including the use ofconformationally restricted furanosyl donors.