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

Author:

Baer Erich,Basu Hemendra

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.

Publisher

Canadian Science Publishing

Subject

General Medicine

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