2- Deoxy-2,2-difluoro-D-ribose

Fig. 31. Synthesis of 2-deoxy-2,2-difluoro-D-ribose from o-pyranoses [96],...

To a solution of 46 mg (0.11 mmol) of 4,6-di-0-benzoyl-3-deoxy-3,3-difluoro-a/p-D-gluco-pyranoside in water-dioxane 1 2 (2 ml) was added 120 mg (0.56 mmol) of sodium periodate. This resulting solution was stirred at room temperature for 20 h. Then, more sodium periodate (55 mg, 0.26 mmol) was added and stirring was continued for 6 h. After that, the solvents were evaporated and the solid was repeatedly extracted with ethyl acetate (total volume 70 ml). The solvent was then evaporated to give a solid that was treated for 15 min with a diluted (0.1%) methanolic solution of ammonia. THE solution was evaporated and the crude purified by preparative TLC (hexane/ethyl acetate 2 1) to yield 18 mg (0.04 mmol, 43%) of a-3,5-di-0-benzoyl-2-deoxy-2,2-difluoro-D-ribose. 

R. Fernandez, M.l. Matheu, R. Echarri, S. Castillon, Synthesis of 2-deoxy-3,5-di-0-benzoyl-2,2-difluoro-D-ribose from D-glucose and D-mannose. A formal synthesis of gemcitabine. Tetrahedron 54 (1998) 3523-3532. 

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