Solution and solid-state structure of N-acetamido-3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosylamine
- PMID: 15178386
- DOI: 10.1016/j.carres.2004.03.025
Solution and solid-state structure of N-acetamido-3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosylamine
Abstract
High resolution 1H NMR and 13C NMR spectroscopic and single crystal X-ray structural analyses of N-acetamido-3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosylamine (1), a minor product of azidonitration reaction of 3,4,6-tri-O-acetyl galactal, are reported. The solution phase studies of 1 reflect that the compound exists in 4C1 conformation with cis-orientation of the substituents at C-1 and C-2. The solid-state structure of 1 reveals that a molecule of water is entrapped in the solid state of 1 and this water molecule serves to mediate N-H...O and C-H...O interactions.
Copyright 2004 Elsevier Ltd.
Similar articles
-
Synthesis, crystal structure, and high-resolution NMR spectroscopy of methyl 3-azido-2,3-dideoxy-4,6-di-O-p-tolylsulfonyl-alpha-D-xylo-hexopyranoside.Carbohydr Res. 2005 Jan 17;340(1):143-7. doi: 10.1016/j.carres.2004.10.016. Carbohydr Res. 2005. PMID: 15620677
-
Syntheses of T(N) building blocks Nalpha-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl)-L-serine/L-threonine pentafluorophenyl esters: comparison of protocols and elucidation of side reactions.Carbohydr Res. 2005 May 23;340(7):1273-85. doi: 10.1016/j.carres.2005.02.029. Carbohydr Res. 2005. PMID: 15854597
-
Crystal structure and solid-state 13C NMR analysis of N-p-nitrophenyl-alpha-D-ribopyranosylamine, N-p-nitrophenyl-alpha-D-xylopyranosylamine, and solid-state 13C NMR analysis of N-p-nitrophenyl-2,3,4-tri-O-acetyl-beta-D-lyxopyranosylamine and N-p-nitrophenyl-2,3,4-tri-O-acetyl-alpha-L-arabinopyranosylamine.Carbohydr Res. 2005 Dec 12;340(17):2645-53. doi: 10.1016/j.carres.2005.09.009. Epub 2005 Sep 29. Carbohydr Res. 2005. PMID: 16199023
-
Conformations of methyl 2,5-di-O-acetyl-beta-D-glucofuranosidurono-6,3-lactone and 1,2,5-tri-O-acetyl-beta-D-glucofuranurono-6,3-lactone in the crystal structure and in solution.Carbohydr Res. 2006 Sep 25;341(13):2275-85. doi: 10.1016/j.carres.2006.06.008. Epub 2006 Jul 12. Carbohydr Res. 2006. PMID: 16839525
-
Azidochrolination reaction of tri-O-acetyl-D-galactal.2021 Oct 23 [updated 2022 Mar 13]. In: Nishihara S, Angata K, Aoki-Kinoshita KF, Hirabayashi J, editors. Glycoscience Protocols (GlycoPODv2) [Internet]. Saitama (JP): Japan Consortium for Glycobiology and Glycotechnology; 2021–. 2021 Oct 23 [updated 2022 Mar 13]. In: Nishihara S, Angata K, Aoki-Kinoshita KF, Hirabayashi J, editors. Glycoscience Protocols (GlycoPODv2) [Internet]. Saitama (JP): Japan Consortium for Glycobiology and Glycotechnology; 2021–. PMID: 37590634 Free Books & Documents. Review. No abstract available.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Miscellaneous