Collect. Czech. Chem. Commun.
2002, 67, 622-644
https://doi.org/10.1135/cccc20020622
Synthesis and Conformation of 6-Amino-3,6-dideoxyhexono-1,6-lactams
Michaela Hamerníkováa,*, Jaroslav Havlíčekb, Hana Votavovác and Karel Kefurta
a Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Prague, 166 28 Prague 6, Czech Republic
b Department of Analytical Chemistry, Institute of Chemical Technology, Prague, 166 28 Prague 6, Czech Republic
c Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
Abstract
Three isomeric 6-amino-3,6-dideoxyhexono-1,6-lactams of D-ribo (1a), L-lyxo (2a) and L-arabino (3a) configuration were synthesized via the corresponding 6-azido-3,6-dideoxyhexoses starting from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose. Conformation of lactams 1a, 2a and 3a and their tri-O-acetyl derivatives 1b, 2b and 3b was studied using NMR spectroscopy. CD spectra of the lactams 1a-3a, together with the D-xylo diastereoisomer 4a, were measured and interpreted according to semiempirical rules. NMR and CD measurements confirmed the chair conformation with an equatorial substituent on C-2 as prevailing for the all measured lactams.
Keywords: Carbohydrates; Lactams; Amino sugars; Conformation analysis; NMR spectroscopy; Circular dichroism.
References: 38 live references.
