Stereoselective synthesis of chirally deuterated (S)-d-(6-2H1)glucose Original Research Article

Chirally deuterated (S)-d-(6-2H1)glucose has been prepared in good overall yield from d-(6,6′-2H2)glucose by a short, five-step synthesis from d-(6,6-2H2)glucose utilizing (R)-(+)-Alpine-Borane® [(R)-9-[(6,6-dimethylbicyclo[3.1.1]hept-2-yl)methyl]-9-borabicyclo[3.3.1]nonane]. Suitably protected methyl 2,3,4-tri-O-benzyl-d-(6,6-2H2)glucopyranoside was prepared and the deuterated O-6 primary alcohol was oxidized to an aldehyde by Swern oxidation. Stereoselective reduction with nondeuterated (R)-(+)-Alpine-Borane® gave methyl 2,3,4-tri-O-benzyl-(6S)-d-(6-2H1)glucopyranoside, which was deprotected under standard conditions to afford the title compound. The key stereoselective reduction step was achieved in 90% yield. The preparation uses economical, commercially available starting materials and will be useful for elucidating biosynthetic mechanisms.