Fluorocarbohydrates. Part XII. Synthesis of cis-iodoglycosyl fluorides by iodofluorination of acetylated glycals

Abstract

The elements of iodine monofluoride have been added to tri-O-acetyl-D-glucal giving two epimeric cis-iodofluorides. The structure of the major product was shown to be tri-O-acetyl-2-deoxy-2-iodo-β-D-mannopyranosyl fluoride by methanolysis to the known alkali-resistant, methyl 2-deoxy-2-iodo-α-D-mannopyranoside, characterised as its benzylidene derivative. Catalytic reduction of the iodo-glycoside, followed by acidic hydrolysis, led to 2-deoxy-D-glucose, isolated as the benzylphenylhydrazone.

The minor adduct was shown to be tri-O-acetyl-2-deoxy-2-iodo-α-D-glucopyranosyl fluoride. The analogous addition reaction with 3,4-di-O-acetyl-D-arabinal has been explored.