Synthesis of β-O-4 linked model oligolignol with a selectively deuterium-labelled methoxy group at the phenolic terminal unit

A lignin model oligomer with only β-O-4 linkages and a selectively deuterium-labelled methoxy group at the phenolic terminal units was synthesised to clarify the behaviour of the phenolic end of oligolignols. First, t-butoxycarbonylmethyl vanillin was synthesised and oligomerised by nucleophilic addition, a known method. The terminal of the oligomers was then subjected to nucleophilic addition to [3-OCD3]benzyl vanillin to achieve selective labelling of the terminal units. A deuterium-labelled lignin model oligomer (D-LM) was obtained through debenzylation and subsequent reduction. The results of thioacidolysis after methylation revealed that the degree of polymerisation was about five, and the deuterium-labelled phenylpropane unit was located only at the phenolic terminal moiety.