Carbohydrate Research p. 21 - 30 (1983)
Update date:2022-08-04
Topics:
Rasmussen, James R.
Tafuri, Sherrie R.
Smale, Stephen T.
Addition of potassium cyanide to 2-deoxy-2-fluoro-D-arabinose (1) at pH 7.8 followed by catalytic hydrogenation over palladium-barium sulfate (5percent) produced 3-deoxy-3-fluoro-D-glucose (4) and 3-deoxy-3-fluoro-D-mannose (5) in 25 and 40 percent isolated yields, respectively.The epimeric sugars were purified by passage through a column of Dowex-50W x 8 (Ca2+).In a similar manner, 3-deoxy-3-fluoro-D-arabinose (6) was converted into 4-deoxy-4-fluoro-D-glucose (9) and 4-deoxy-4-fluoro-D-mannose (10) in 27 and 45 percent isolated yields, respectively.Deoxyfluorohexoses 4,5,9 and 10 enriched with carbon-13 and crbon-14 at C-1 have been prepared by this procedure.
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