Fluorocarbohydrates. Part XIII. Synthesis of 2-deoxy-2-fluoro-(±)-glyceraldehyde 3-O-phosphate

Abstract

2-Deoxy-2-fluoro-(±)-glyceraldehyde has been characterised as a crystalline (–)-menthyl hydrazone and purified as the relatively stable diethylacetal. Treatment of the latter with diphenyl phosphorochloridate followed by catalytic hydrogenation gave the corresponding 3-O-phosphate, which was isolated as the crystalline bis-cyclo-hexylammonium salt.

Preliminary investigations indicate that the fluoroglyceraldehyde phosphate is not a powerful inhibitor of rabbit muscle triose phosphate dehydrogenase.