Synthesis of Pyridinium Dinitrobenzyl Sulfates and Potassium (Dinitrobenzyl β-D-Glucopyranosid)Uronates

Abstract

Sulfates and glucuronides of 2, 4-dinitrobenzyl alcohol 1a and 2, 6-dinitrobenzyl alcohol 1b, which are major or putative metabolites of 2, 4-dinitrotoluene (2, 4-DNT) and 2, 6-dinitrotoluene (2, 6-DNT), were synthesized from 1a and 1b by reaction with pyridinium sulfonate and methyl (2, 3, 4-tri-O-acetyl-α-D-glucopyranosyl)uronate bromide 3, respectively, as their pyridinium salts (2a, 2b) and potassium salts (6a, 6b). These conjugates are important for the study of the carcinogenicity of 2, 4-DNT and 2, 6-DNT.