Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected 1-C-Me GlcNAc oxazoline, a potential 1-C-Me GlcNAc donor.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry