Phosphorylated sugars. Part 23. Synthesis and reactions of phosphodiesters containing 2-aminoethanol and a polyfunctional alcohol and their behaviour during acid- and base-catalysed hydrolysis

Abstract

Phosphodiesters of 2-aminoethanol and of polyhydroxylated alcohols and sugars have been synthesised; their behaviour in M-HCl and in saturated (ca. 0.2M) Ba(OH)₂ solutions at 100 °C have been examined. With the exception of 2-aminoethyl ethyl phosphate which, in acidic medium, yielded 2-aminoethylphosphate, free 2-aminoethanol and phosphorylated polyols or sugars were the main products formed. Because of simultaneously and/or sequentially occurring reactions the structures of the phosphorylated derivatives formed gave no unambiguous information regarding the structure of the initial phosphodiester.