Synthesis of D-glucose-1-C-14 and D-mannose-1-C-14

Abstract

The cyanohydrin, D-arabinose synthesis of D-glucose-1-C14 was investigated stepwise and modified, resulting in about 50% yields on a millimolar level. Condensation of D-arabinose with cyanide is nearly quantitative under a variety of conditions. Milder cyanohydrin hydrolysis avoids decomposition. Gluconic mannonic acid yields are variable by alteration of conditions. The delta lactone, on reduction with Na amalgam, gives the sugar more readily than the gamma lactone. pH is maintained during lactone reduction using difficultly soluble, solid organic acid in excess. Radio-chemical yields of the several products from D-arabinose obtained when using the recommended procedures are tabulated.