An improved synthesis for obtaining 2-deoxy-2-iodo-D-mannopyranose derivatives

Abstract

The aim of this work was to synthesize 2-deoxy-2-iodo-manno sugars and 2-deoxy-2-iodo manno esters of a satisfactory purity in the highest possible yield. For this purpose, the iodination reaction of D-glucal triacetate (1), 3,4-di-O-acetyl-6-O-to-syl-D-glucal (2) and 3,4-di-O-acetyl-6-S-acetyl-6-thio-D-glucal (3) were investigated using a mixture of NaIO 4 -NaI at pH 6 (acetate buffer) and pH 7 (phosphate buffer) in a tert-butanol-water solvent system. Depending on the buffer system used, a mixture of the 2-deoxy-2-iodo-manno esters 4, 6 or 8 together with corresponding 2-deoxy-2-iodo sugars 5, 7, or 9 were obtained, or separately.