Synthetic strategies for fluorination of carbohydrates

Abstract

Different synthetic strategies for accomplishing regio- and stereoselective fluorinations of carbohydrate scaffolds are discussed in light of the biological implications arising from such substitutions.

Diethylaminosulfur Trifluoride (DAST) Mediated Transformations Leading to Valuable Building Blocks and Bioactive Compounds

“…[68] Recently, the fluorination of carbohydrates and their derivatives has been successfully applied to improve the activity of drug candidates and already used drugs. [70] Introduction of a CF 2 or CHF group, as isosteres of oxygen, modifies the pK a of the adjacent groups, and can increase the lipophilicity of the molecules. Introduction of CF 2 into the anomeric position is a known method, but the research is still ongoing to learn about other approaches, more selective and efficient.…”

Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose

“…The synthesis of complex polyfluorinated carbohydrates is challenging and new synthetic methods must be developed. Pioneering work by many groups brought significant progress to the development of innovative synthetic methodology to access polyfluorosugars [18]. For our part, we recently de- scribed the preparation of multi-vicinal trifluorinated hexopyranose analogues 6-9 using the Chiron approach from levoglucosan (1, Figure 1) [19].…”

Enzymatic glycosylation involving fluorinated carbohydrates

“…The review of Li, McArthur and Chen 14 provides an excellent summary of chemical and enzymatic transformations using natural and synthetic sugars. The reviews of Uhrig and Guo et al [15][16] provide overviews of synthetic strategies for fluorination of carbohydrates and methods of introducing stereoselective fluorination into monosaccharide structures. Enzymatic synthesis of fluorosugars has however not previously been the subject of a focussed extensive review.…”