Synthesis and structure of 6-amino-2,3,6-trideoxy-d-erythro-hexono-1,6-lactam and 6-amino-3,6-dideoxy-d-xylo-hexono-1,6-lactam Original Research Article

Solid-state conformations of 6-amino-2,3,6-trideoxy-d-erythro-hexono-1,6-lactam (3a) and 6-amino-3,6-dideoxy-d-xylo-hexono-1,6-lactam (7a) were determined using X-ray diffraction. Conformations of the compounds 3a, 7a, and their per-O-acetyl derivatives 4,5-di-O-acetyl-6-amino-2,3,6-trideoxy-d-erythro-hexono-1,6-lactam (3b) and 2,4,5-tri-O-acetyl-6-amino-3,6-dideoxy-d-xylo-hexono-1,6-lactam (7b) in solutions were deduced from the analysis of NMR spectra using a modified Karplus equation and compared with the results of circular dichroism measurement of lactams 3a and 7a. Conformation 4C1,N was revealed for solid lactams 3a and 7a and for lactams 7a and 7b in solution, while lactams 3a and 3b in solution exist in the ∼1:1 equilibrium of the conformers 4C1,N and 1,NC4.