Organic Phosphates. XII. Hydrobenzoin Cyclic Phosphoro-chloriodate as a Phosphorylating Agent.

Abstract

Hydrobenzoin cyclic phosphorochloridate was synthesized and isolated in a pure state. This compound was reacted with 2-(benzyloxycarbonylamino) ethanol, 1, 2, 3, 4-tetra-O-acetyl-β-D-glucose, and 2', 3'-O-isopropylideneadenosine, and the reaction products were submitted to hydrogenolysis to obtain the respective O-phosphate of the above three alcoholic compounds. Removal of the protective group from the phosphates thus obtained gave phosphorylethanolamine, D-glucose 6-phosphate, and adenosine 5'-phosphate, respectively.