Advances in Organic Synthesis

Volume: 2

Fluorinated Carbohydrates

Author(s): Martin Hein and Ralf Miethchen

Pp: 381-429 (49)

DOI: 10.2174/978160805198410602010381


The review demonstrates how carbohydrate chemists exploit the two fundamental strategies of organofluorine chemistry; (a) direct introduction of fluorine atom(s) or fluorinated groups by appropriate reagents in a late synthetic step, or (b) linking of fluorine-containing “building blocks“ with various reactants (including enantioselective approaches), in order to synthesize a wide variety of fluorinated sugars. Numerous representative examples of these strategies are provided and discussed. Also included are a number of recommended experimental procedures (provided at the end of sections 1-3). In addition to reviewing various convenient fluorinating reagents that have so far been applied to carbohydrate chemistry, the utility of glycosyl fluorides in chemical and enzymatic glycosylations are also examined.

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