Glucose 2-deoxy-2-fluoro

Deoxy-2-[18F]fluoro-D-glucose (labelled) or (2fl)-2-deoxy-2-[18F]fluoro-D-arab/no-hexose... 

Syntheses of 3-deoxy-3-fluoro sugars are described next. A rapid synthesis aimed at 3-deoxy-3-[ F]fluoro-D-glucose ( F-3DFG) was developed. ... 

Deoxy-5-fluoro-D-glucose and -L-idose were synthesized from 1,2-(9-isopropylidene-a-D-glucofuranurono-6,3-lactone (285). Treatment of l,2-0-isopropylidene-5-0-triflyl-a-D-gluco- (286 prepared from 285) and -) -L-ido-furanurono-6,3-lactones (289 prepared from 288), with BU4NF... 

Deoxy-3-fluoro-D-glucose (25%) and -mannose (40%) were prepared from 2-deoxy-2-fluoro-D-arabinose by a chain-extension reaction (cyanohydrin synthesis). Likewise, 4-deoxy-4-fluoro-D-glucose ° (27%) and -mannose (45%) were prepared from 3-deoxy-3-fluoro-D-arabinose. ... 

Coe and Bessell and coworkers studied the metabolic fates of 2-deoxy-2-fluoro-D-glucose (2DFG) and related compounds by using yeast hexokinase (as a model for mammalian hexokinase), and determined the kinetic constants K and V ) of the Michaelis-Menten equation D-glucose 0.17 (K in mAf)> 1 00 (relative value, D-glucose taken as 1) 2DG 0.59 0.11, 0.85 2DFG 0.19 0.03, 0.50 2-deoxy-2-fluoro-D-mannose (2DFM) 0.41 0.05, 0.85 2-deoxy-2,2-difluoro-D-nraZ>//Jo-hexose... 

Deoxy-3-[ F]fluoro-D-glucose ( F-3DFG) was prepared - 454,467,473-476 essentially according to the procedure for the cold synthesis (see Section 11,2), namely, treatment of248 with Cs F (in DMF or HMPA), tetraalkylammonium [ F]fluoride (DMF, HMPA, or MeCN) or K F (in acetamide). 6-Deoxy-6-[ F]fluoro-a-D-galactopyranose was likewise pre-pared aceording to the cold synthesis. ... 

The incorporation and metabolism of 2-deoxy-2-fluoro-D-[ H]glucose and -D-[ H]mannose in yeast and chick-embryo cells has been studied. 2-Deoxy-2-fluoro-D-glucose, 2-deoxy-2-fluoro-D-mannose, and their GDP and UDP derivatives were found to interfere with protein (involving that of... 

Deoxy-3-fluoro-D-glucose (see Section 11,2), a weak substrate for yeast hexokinase, is phosphorylated enzymically - to give the 6-phosphate 588, which is transformed into 2-deoxy-2-fluoro-D-arabinose 5-phos-phate (589) by lead tetraacetate oxidation. 

Volkow ND, Gillespie H, Mullani N, Tancredi L, Grant C, Ivanovic M, Hollister L. Cerebellar metabolic activation by delta-9-tetrahydrocannabi-nol in human brains. A study with positron emission tomography and 18F-2-deoxy-2-fluoro-D-glucose. Psychiat Res 1991 40 69-80. 

Formation of the oxazoline reduced undesirable 18F-19F exchange and the desired product was rapidly (15s) isolated in good yield (45-55%) with a specific activity (1.1 GBq pmol-1) that was 20 times higher than that obtained when using direct debromination route. In another example, the synthesis of 2-deoxy-2-18F-fluoro-D-glucose [110] the high purity of the product and the improved specific activity is attributed to the short reaction times that are made possible via the use of micro-... 

Potassium fluoride in 1,2-ethanediol has further been used, as, for example, in the preparation of 5-deoxy-5-fluoro-D-ribose from methyl 2,3-0-isopropylidene-5-0-(methylsulfonyl)-a-D-ribofuranoside,87 and of 6-deoxy-6-fluoro-D-glucose from methyl 6-O-p-tolylsulfoiiyl-a-D-glucopyranoside.77 In one study of primary fluorinations with potas-... 

The availability, in gram quantities, of the fluorinated carbohydrates thus far synthesized has also made possible their use as starting materials for the synthesis of other analogs and intermediates for example, the preparation of 3,5-dideoxy-3,5-difluoro-D-xylose from 3-deoxy-3-fluoro-D-xylose,88 which is itself preparable from 3-deoxy-3-fluoro-l,2-0-isopropylidene-a-D-glucofuranose. Electrolytic oxidation of 3-deoxy-3-fluoro-D-glucose afforded, after treatment with an acidic... 

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