Synthesis of C-13-labeled biosynthetic precursor of lipid A and its analogue with shorter acyl chains

The synthesis of regiospecifically C-13-labeled compounds of a biosynthetic precursor of lipid A and its analogue with shorter acyl chains is describe d. D-(6-C-13)Glucose was converted into a suitably protected glucosamine de rivative via 1,6-anhydro-beta-D-(6-C-13)glucose. After coupling with glycos yl donors, the desired compounds were synthesized through a 6-step reaction sequence. The total yields were 1.7% for the biosynthetic precursor, and 6 .4% for the short acyl analogue, respectively, for a total of 18 steps from D-(6-C-13)glucose.