Perfluoroalkyl sugar

In this chapter, fluorinated saccharidic compounds are considered in the following order fluorinated analogues of furanoses and nucleosides, followed by pyranoses and then fluoromethylated sugars. Finally, a brief summary of perfluoroalkylated sugars and of their amphiphilic properties is given. 

Perfluoroalkyl sugars have been designed to facilitate the transport of a drug (e.g., arabinocytosine). The linking element, in this case, is a biodegradable function. ... 

Zhu W, Li ZY (2(X)0) Synthesis of perfluoroalkylated sugars catalyzed by rabbit muscle aldolase (RAMA) J Chem Soc Perkin Trans 17 1105-1108... 

The presence of long perfluoroalkyl chains gives sugars surfactant and emulsifier properties, with interesting applications in the biomedical field. These applications... 

Perfluoroalkyl tail Hydrocarbon linker Junction spacer Polar head Figure 6.48 Creation of fluorinated surfactant derived from a sugar. 

The diacetone-D-glucosyl-3-0-(A A -diethylamido)thiophosphates of the lipid-soluble vitamins D2, D3, and E have been obtained in a one-pot procedure by sequential addition of the vitamin, the sugar, and sulfur to phosphorous acid tris(A,A -diethyl)amide in the presence of catalytic iodine. In the preparation of the 3-[sodium-2-(perfluoroalkyl)ethyl phosphates] 47 of diacetone glucose. 

Overall, the tetrazole transformation methodology is a quite general approach. Almost any nitrile can be transformed into the corresponding tetrazole precursor which can lead to a perfluoroalkyl-l,3,4-oxadiazole. One example is represented in Scheme 25 for sugar-linked system 85 obtained from the corresponding D-glucose tetrazole derivative (Scheme 25) [44],... 

There are several other methods for generation of (per)fluoroalkyl radicals in reactions with diazines. In particular, photochemical decomposition of perfluoroalkyl mercury derivatives was used for perfluoroalkylation of uracils 568 (Scheme 120) [297]. Whereas for the parent uracil the method gave satisfactory results (30-54 % yields), the procedure was unfruitful for the sugar-modified derivatives (6-11 % yields). 

Polymeric fluorinated surfactants (1) have a fluorinated backbone or (2) contain perfluroalkyl groups, as pendant perfluoroalkyl groups attached directly or indirectly to the polymer backbone, or as one or two fluorinated end groups of the polymer. A perfluoroalkyl tail can be attached to poly(tris(hydroxymethyl)-acrylamidomethane or to a natural product, such as a sugar, polyol, and so forth [180]. A fluorinated group may be attached to a poly(oxyethylene) chain —CH2CH2O—, to an ethylene oxide-propylene oxide block polymer, or to an acrylic comonomer. 

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