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

Michaela Hamerníková, University of Chemistry and Technology, Prague
Svetlana Pakhomova, University of Chemistry and Technology, Prague
Jaroslav Havlíček, University of Chemistry and Technology, Prague
Hana Votavová, Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic
Karel Kefurt, University of Chemistry and Technology, Prague

Abstract

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 4C(1,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 4C(1,N) and (1,N)C4. Copyright (C) 2000 Elsevier Science Ltd.