Regioselective synthesis of 1I,1II,5I,5II,6I,6I,6II,6II-2H8-cellobiose

Partially deuteriated 1,5,6,6-2H4-d-glucose and 1I,1II,5I,5II,6I,6I,6II,6II-2H8-d-cellobiose were synthesized in high yields and on a large scale from d-glucose. 2H enrichment at C-5 and C-6 of each glucopyranosyl unit in excess of 85% and 90%, respectively, was realized by 1H–2H exchange in 2H2O containing deuteriated Raney Ni. Nucleophilic addition of LiAlD4 to 5,6,6-2H3-2,3,4,6-tetra-O-benzyl-d-gluconolactone led to a 98% 2H enrichment at C-1. Deuteriated cellobiose is of interest as building block for the synthesis of a model compound of cellulose I.

Figure optionsDownload as PowerPoint slide