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

Abstract
D-Glucose-3-14C 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-1-14C and d-erythrose-1-14C: (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- 14 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-3-14C 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.