Carbohydrates are one of the three most important components of living cells (the other two being amino acids and lipids). Two properties of carbohydrates that are most important for their chemical behavior are their shape (conformation) and stereoelectronic interactions that are unique and characteristic for each carbohydrate structure. Carbohydrates containing trifluoromethyl groups may be regarded as very useful tools, e.g. for in vivo 19F NMR spectroscopy or for other biomedical purposes. The conformation of active pharmaceutical ingredients (APIs) is the key factor responsible for docking of API molecules in proteins and for their therapeutic performance. Therefore methods of controlling the conformation of API molecules may be useful for obtaining new effective drugs. The subject of this presentation will be the synthesis of fluorinated and polyfluorinated carbohydrate derivatives and the study of spectroscopic and electronic properties of newly obtained compounds. In particular studies of fluorinated vinyl ethers from di-O-isopropylidenehexofuranose, O-Isopropylidenepentofuranose and O-isopropylideneglyceraldehyde will be reported. Similarly, preparation of fluorinated building blocks for the synthesis of modified hyaluronic acid subunits has been carried out. As a special approach to build fluorinated analogues of sugars 1,3–dipolar cycloaddition has been tested.

Fluorinated sugars: Formulation of customized cannabis concentratesaluable building blocks and chiral tools in organic synthesis

2019 Spring National Meeting

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