Carbohydrate Research

Synthesis of 3-deoxy-3-fluoro-d-mannose and 4-deoxy-4-fluoro-d-mannose

JR Rasmussen, SR Tafuri, ST Smale

Index: Rasmussen, James R.; Tafuri, Sherrie R.; Smale, Stephen T. Carbohydrate Research, 1983 , vol. 116, p. 21 - 30

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Citation Number: 7

Abstract

Abstract Addition of potassium cyanide to 2-deoxy-2-fluoro-d-arabinose (1) at pH 7.8 followed by catalytic hydrogenation over palladium—barium sulfate (5%) produced 3-deoxy- 3-fluoro-d-glucose (4) and 3-deoxy-3-fluoro-d-mannose (5) in 25 and 40% isolated yields, respectively. The epimeric sugars were purified by passage through a column of Dowex- 50W× 8 (Ca 2+). In a similar manner, 3-deoxy-3-fluoro-d-arabinose (6) was converted into ...