Synthesis of d-Glucose-3-¹⁴ C and Related Compounds

d-Glucose-3-¹⁴ C has been prepared by means of three, successive Kiliani syntheses. The process consists of (a) the addition of ¹⁴C-labeled-cyanide to d-glyceraldehyde; (b) hydrolysis of the cyanohydrins and conversion of the resulting epimeric d-tetronic-1-¹⁴C acids into d-tetroses-1-¹⁴C by way of an improved Rosenmund reduction of the acetylated tetronyl chlorides: (c) addition of nonlabeled cyanide to the mixture of the aldehydo acetates of d-threose-1-¹⁴ C and d-erythrose-1-¹⁴ C: (d) hydrolysis of the cyanohydrins, and lactonization of the resulting mixture of four d-pentonic-1-¹⁴C acids; (e) chromato-graphic separation of these into three fractions; (f) reduction of the fraction containing d-arabinono-2- C- and d-xylono-2-¹⁴C-lactone to the corresponding sugars, and chromatographic separation of these; and (g) conversion of d-arabinose-2-¹⁴C into d-glucose-3-¹⁴C and d-mannose-3-¹⁴ C by a third Kiliani synthesis. Approximately 3 percent of the radioactivity was obtained in the form of d-glucose-3-¹⁴C The process results in the production of a large number of intermediate labeled compounds.