Stereoselective synthesis of chirally deuterated (S)-D-(6- 2H1)glucose

Article abstract of DOI:10.1016/j.carres.2004.02.010

Chirally deuterated (S)-D-(6-²H₁)glucose has been prepared in good overall yield from D-(6,6′-²H ₂)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.