Phosphonic acid analogues of carbohydrate metabolites. I. Synthesis of L- and D-dihydroxypropylphosphonic acid

Abstract

A synthesis of the phosphonic acid analogues of L-α- and D-α-glycerophosphoric acid, viz. L- and D-dihydroxypropylphosphonic acid, is described. The L-dihydroxypropylphosphonic acid was obtained by treating acetone α-iodo-L-propylene glycol with triethyl phosphite at 120–125° for 24 h, hydrolyzing the condensation product acetone L-dihydroxypropylphosphonic acid diethyl ester with 2 N sulfuric acid at 100° for 48 h, and isolating the L-dihydroxypropylphosphonic acid as barium salt. The D-dihydroxypropylphosphonic acid was prepared in the same manner from acetone α-iodo-D-propylene glycol. The barium salts are readily soluble in cold water, much less soluble in hot water, and insoluble in the more common organic solvents. Dihydroxypropylphosphonic acid and α-glycerophosphoric acid can be distinguished from each other by their different behaviors towards hot mineral acids, and by the infrared spectra, n.m.r. spectra, and optical rotations of their barium salts.