Synthesis of Individually Protected Monosaccharides from C1-Building Blocks

• Applicant: Dr. Christoph Hirschhäuser
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2017 to 2021
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 371758729

The objective of this project is the development of a diastereodivergent synthesis for monosaccharide building blocks, based on Matteson-homologations. Since this approach involves the stereoselective assembly of the target molecules almost atom by atom, a maximum of variability should result that would also pave the way for future syntheses of chiral scaffolds beyond classical carbohydrates. However, boronate homologations of heteroatom-rich systems are often challenging. Based on examples from the literature, as well as our own experience, we hypothesize that the formation of cyclic adducts can inhibit the reactivity of oxygen-rich systems. This challenge is to be addressed by the choice of appropriate chiral directors or routes that avoid such problematic intermediates. Furthermore, efficient routes to all stereoisomers are to be explored, as well as a new method for the covalent coupling of two appropriate building blocks under stereoselective formation of an orthogonally protected glycol-motif.

• DFG Programme: Research Grants