A clean conversion of d-glucosamine hydrochloride to a pyrazine in the presence of phenylboronate or borate
2001
Abstract
D-Glucosamine was found to undergo a condensation to give 2-(arabo-tetrahydroxybutyl)-5-(erythro-2,3,4-trihydroxybutyl)-pyrazine (2) as practically the sole product in the presence of phenylboronate or borate. The reaction proceeds in aqueous solutions at room temperature in 3 h in 58% isolated yield.
In D2O solutions, the incorporation of one deuterium into the methylene group of the trihydroxybutyl arm was found. The borate esters of the product were investigated by 11B and 13C NMR spectroscopy.