J. Rohovec et al., Clean conversion of D-glucosamine hydrochloride to a pyrazine in the presence of phenylboronate or borate, EUR J ORG C, (20), 2001, pp. 3899-3901
D-Glucosamine was found to undergo a condensation to give 2-(arabo-tetrahyd
roxybutyl)-5-(erythro-2,3,4-trihydroxybutyl)-pyrazine (2) as practically th
e sole product in the presence of phenylboronate or borate. The reaction pr
oceeds in aqueous solutions at room temperature in 3 h in 58% isolated yiel
d. In D2O solutions, the incorporation of one deuterium into the methylene
group of the trihydroxybutyl arm was found. The borate esters of the produc
t were investigated by B-11 and C-13 NMR spectroscopy.